Name: 897921-59-4|N-(4-(Naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine|98%
Brand: Ambeed
SKU: A582799
Rating: 99 (22 reviews)

Yield	Reaction Conditions	Operation in experiment
89.7%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane In toluene at 65 - 75℃; for 1h; Inert atmosphere;	1.3 (3) Synthesis of intermediate D-1 General procedure: Pour nitrogen (0.100L/min) into a three-necked flask equipped with mechanical stirring, thermometer and spherical condenser for 15 minutes. Add reactant NM-1 (20g, 106mmol), reactant P-1 (10.4g, 112mmol), toluene (200mL), and raise the temperature to 65-75 °C. Then, add sodium tert-butoxide (15.2g, 158mmol), X-Phos (0.88g, 2.12mmol), Pd2(dba)3 (0.98g, 1.06mmol) in sequence. Turn on stirring, heat and reflux for 1h. After the reaction, it was cooled to room temperature. After the reaction solution is washed with water, the organic phase is separated, and the organic phase is dried with anhydrous magnesium sulfate, and after filtration, the filtrate is concentrated by distillation under reduced pressure to obtain a crude product;The crude product was purified by silica gel column chromatography to obtain intermediate D-1 (22.6 g, yield 86.9%).
78.7%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane In toluene at 70 - 110℃; for 1h; Inert atmosphere;	7 7. Synthesis of intermediate IM D-1 General procedure: Under a nitrogen atmosphere, put 4-bromo-p-terphenyl (23.3g, 75.5mmol), aniline (7.03g, 75.5mmol), 150mL of ultra-dry toluene into a 250mL three-necked flask, heat up to 70°C, and sequentially add sodium tert-butoxide (10.9g, 113.3mmol), X-Phos (0.63g, 1.51mmol), Pd2(dba)3 (0.70g, 0.76mmol), then the temperature was raised to 110° C. for reflux reaction for 1h, cooled to room temperature, and the reaction solution was washed three times with water , dried with anhydrous magnesium sulfate, allowed to stand for 30 min, suction filtered, concentrated under reduced pressure, and passed through a column chromatography column to obtain IM D-1 (19.5 g, yield 80.2%).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 80℃; for 5h;	Synthesis of Intermediate I-18 General procedure: 14.3 g (100.0 mmol) of 1-aminonaphthalene, 23.3 g (100.0 mmol) of 4-bromobiphenyl, 4.6 g (5.0 mmol) of Pd2(dba)3, 1.0 g (5.0 mmol) of P(tBu)3, and 14.4 g (150.0 mol) of NaOtBu were dissolved in 300 mL of toluene, and the reaction solution was stirred at 80° C. for 5 hours. The reaction solution was cooled to room temperature, 300 mL of water was added thereto, and an organic layer was extracted using 300 mL of diethyl ether three times. The organic layer thus collected was dried with magnesium sulfate, the magnesium sulfate was removed by filtration, and the residue obtained after evaporating a solvent therefrom was separated and purified using silica gel column chromatography to obtain 26.0 g of Intermediate I-18 (yield: 88%). The compound thus produced was identified by LC-MS. (0290) C22H17N: M+1 296.1

	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 100℃;	Examples of Sub 2-1 General procedure: Examples of Sub 2-1 (0055) (0056) After Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd2(dba)3 (7.37 g, 8.05 mmol), P(t-Bu)3 (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), and toluene (1690 mL) are added in a round bottom flask, stirring at 100° C. When the reaction is complete, the product was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated, and then the product was separated by a silicagel column chromatography and recrystallized to obtain 25.4 g of product Sub 2-1 (yield: 72%).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 100℃;	1 Example of Sub 2-1 General procedure: A round bottom flask was charged with aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd2(dba)3 (7.37 g, 8.05 mmol), P(t-Bu)3 (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 mL) is added and the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 25.4 g of Sub 2-1. (Yield: 72%).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 100℃;	1 [Example of Sub 2-1] General procedure: Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd2 (dba) 3 (7.37g, 8.05 mmol), P (t-Bu) 3 (3.26 g, 16.1 mmol) in a round bottom flask ), NaOt-Bu (51.08 g, 531.5 mmol) and toluene (1690 mL) were added followed by reaction at 100 ° C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and the resulting organics were silicagel column and recrystallized to obtain 25.4 g of Sub 2-1. (Yield 72%)
	With tri-tert-butyl phosphine; Palladium⁽⁰⁾ bis(dibenzylideneacetone); sodium tertiary butoxide In toluene at 100℃;	1 [Example of Sub 2-1] General procedure: Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd2(dba)3(7.37 g, 8.05 mmol), P (t-Bu)3(3.26 g, 16.1) mmol), NaOt-Bu (51.08 g, 531.5 mmol) and toluene (1690 mL) were added followed by reaction at 100 ° C.After completion of the reaction, the mixturewasextracted withCH2Cl2and water, the organic layerwas dried overMgSO4and concentrated, and the resulting organics were purified by silicagel column and recrystallized to obtain 25.4 g of Sub 2-1.(Yield 72%)
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 100℃;	1 [Example of Sub 2-1] General procedure: Aniline (15 g, 161.1 mmol) in a round bottom flask,1-bromonaphthalene (36.7 g, 177.2 mmol),Pd 2 (dba) 3 (7.37 g, 8.05 mmol),P (t-Bu) 3 (3.26 g, 16.1 mmol),NaOt-Bu (51.08 g, 531.5 mmol),Add toluene (1690 mL) and proceed with the reaction at 100 ° C.After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and the resulting organics were purified by silicagel column and recrystallized to obtain 25.4 g of Sub 2-1. (Yield 72%)
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 100℃;	1 [Example of Sub 2-1] General procedure: To a round bottom flask was added Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd2(dba)3 (7.37 g, 8.05 mmol), P(t-Bu)3 (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol) and toluene (1690 mL), and the reaction was performed at 100 ° C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain 25.4 g of Sub 2-1. (Yield: 72%)
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium tertiary butoxide In toluene for 7h; Inert atmosphere; Reflux;	11 Synthesis of intermediate C-1: General procedure: Under the protection of nitrogen, toluene solvent (200mL), D-1 (3.72g, 40mmol), E-1 (8.28g, 40mmol), Pd2(dba)3(0.36g, 0.40mmol)were sequentially added to the reaction flask under the protection of nitrogen. , BINAP (0.74g, 1.20mmol) and sodium tert-butoxide (7.68g, 80mmol), stir to dissolve, and reflux for 7 hours under the protection of nitrogen. After the reaction is complete, cool the mixture to room temperature and filter through diatomaceous earth The filtrate was obtained, and the organic solvent was removed from the filtrate by distillation under reduced pressure. The obtained solid material was recrystallized with methanol to finally obtain Intermediate C-1 (7.19 g, yield 82%).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 105℃; for 24h; Inert atmosphere;	1 Example 1: Synthesis of intermediate B1: General procedure: In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol of raw material 1-1, 0.012mol of raw material 2-1, and 150ml of toluene, stir and mix, and then add 5×10-5mol Pd2(dba)3, 5×10-5mol P( t-Bu)3, 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling point plate, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column, Obtain the target product intermediate B1; HPLC purity 98.55%, yield 79.36%;

2
[ 92-66-0 ]
[ 125404-00-4 ]
[ 897921-59-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium t-butanolate In tetrahydrofuran for 0.3h; Inert atmosphere; Reflux;	Synthesis of compound N-[4-(1-naphthyl)phenyl]-[1,1'-biphenyl]-4-amine First of all, the following synthesizing N-[4-(1-naphthyl)phenyl]-[1,1'-biphenyl]-4-amine. In the argon atmosphere, will 4.22g 4-bromobiphenyl, 4.05g 1-(4-aminophenyl)naphthalene, 0.78g (DPPF)PdCl2, 1.60g DPPF and 1.77g NaOtBu is added to 300 ml three-necked flask, after 120 ml of solvent THF heating, reflux and stirring for about 3 hours. After air cooling, adding water, separating organic layer, and distilling solvent. The crude product thus obtained by silica gel column chromatography (using dichloromethane and hexane mixture solvent) separating and the use of a mixture of toluene and ethanol in order to produce the solvent recrystallization 6.31g is the yellow solid of a target product (yield 92%).
83%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	II.1 Synthesis of Sub 2(4) round bottom flask Sub 2-1(1) (4.7g, 20mmol), Sub 2-2(1) (4.4g, 20mmol), Pd2 (dba)3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol ), NaOt-Bu (5.8g, 60mmol), were added to toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100°C. The organic layer was dried over MgSO4, and extracted with water and ether and recrystallized silicagel column and the resulting organic one was concentrated to a Sub 2 (4), 6.2g (Yield: 83%) was obtained.
	In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene	(Synthesis of N-[4-(1-naphthalenyl)phenyl]-[1,1'-biphenyl]-4-amine) (Synthesis of N-[4-(1-naphthalenyl)phenyl]-[1,1'-biphenyl]-4-amine) First, the following N-[4-(1-naphthalenyl)phenyl]-[1,1'-biphenyl]-4-amine was synthesized. Under an Ar atmosphere, 4.22 g of 4-bromobiphenyl, 4.05 g of 1-(4-aminophenyl)naphthalene, 0.78 g of (DPPF)PdCl2, 1.60 g of DPPF and 1.77 g of NaOtBu were added to a 300 mL, three necked flask, followed by heating, refluxing and stirring in 120 mL of a mixture solvent of THF for about 3 hours. After air cooling, water was added, an organic layer was separated, and the solvents were distilled. The crude product thus obtained was separated by silica gel column chromatography (utilizing a mixture solvent of dichloromethane and hexane) and recrystallized utilizing a mixture solvent of toluene and ethanol to produce 6.31 g of a target product as a yellow solid (Yield 92%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - CN105541790, 2016, A Location in patent: Paragraph 0259; 0260; 0261; 0262
[2]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - KR2015/117399, 2015, A Location in patent: Paragraph 0161; 0162; 0163
[3]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2016/118597, 2016, A1

3
[ 897921-59-4 ]
C₂₈H₁₃⁽²⁾H₇BrN [ No CAS ]
C₅₆H₃₃⁽²⁾H₇N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	III.1 Synthesis of 1-4 In a round bottom flask Sub 1(9) (9.1g, 20mmol), Sub 2 (4) (7.4g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt- Bu (5.8g, 60mmol), were added to toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100°C. The organic layer was dried over MgSO4 with water and ether and re-crystallized silicagel column and and the resulting one was concentrated to 1-4 to 11.7g (78% yield)

Reference： [1]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - KR2015/117399, 2015, A Location in patent: Paragraph 0180; 0181; 0182

4
[ 897921-59-4 ]
C₂₄H₁₅BrO [ No CAS ]
C₅₂H₃₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene Inert atmosphere; Reflux;	Scheme 32 synthesis of compound 251 In the argon atmosphere, will 4.79g compound E, 3.71g N-(4-phenylphenyl)phenanthren-9-amine, 0.40g Pd2(dba)3, 0.72g tri-tert-butylphosphine and 2.90g NaOtBu added to the 200 ml three-necked flask, after 87 ml of toluene solvent heating and stirring about 5 hours. After air cooling, adding water, separating organic layer, and distilling solvent. The crude product thus obtained by silica gel column chromatography (using dichloromethane and hexane mixture solvent) separating and the use of a mixture of toluene and ethanol in order to produce the solvent recrystallization 5.50g is a white solid of compound 251 (yield 80%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - CN105541790, 2016, A Location in patent: Paragraph 0342; 0343; 0344; 0345; 0346

5
[ 897921-59-4 ]
C₂₄H₁₅BrO [ No CAS ]
C₅₂H₃₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene Inert atmosphere; Reflux;	Scheme 24 synthesis of compound 170 In the argon atmosphere, will 3.59g compound I, 2.71g N-[4-(1-naphthyl)phenyl]-[1,1'-biphenyl]-4-amine, 0.30g Pd2(dba)3, 0.54g tri-tert-butylphosphine and 2.18g NaOtBu added to the 200 ml three-necked flask, after 65 ml of heated in toluene solvent, reflux and stirring for about 4 hours. After air cooling, adding water, separating organic layer, and distilling solvent. The crude product thus obtained by silica gel column chromatography (using dichloromethane and hexane mixture solvent) separating and the use of a mixture of toluene and ethanol in order to produce the solvent recrystallization 4.19g is the yellow solid compound 170 (yield 81%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - CN105541790, 2016, A Location in patent: Paragraph 0263; 0264; 0265; 0266; 0267

6
[ 897921-59-4 ]
C₂₁H₁₅ClO [ No CAS ]
C₄₉H₃₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In toluene for 12h; Reflux;	9 To a round bottom flask and the intermediate M-21 9.9g (31.5mmol) Biphenyl-4-yl- (4-naphthalen-1-yl-phenyl) -amine11.5g (31.5mmol), put a small diyum t- butoxide 4.5g (46.35mmol) was dissolved in toluene 155ml. HereButylphosphine was placed under the pin 0.125g (0.62mmol) and then nitrogen - Pd (dba) 2 0.178g (0.31mmol) and tri-tertStanding the mixture was stirred under reflux for 12 hours. After the reaction extracted with distilled water and toluene and the organic layer was dried with magnesium sulfate,Filtered, and the filtrate was concentrated under reduced pressure. The product n- hexane / dichloromethane (8: 2 by volume) as a silica gel column chromatographyOf the aimed compound 2-217 compound was purified by chromatography to give the 18.27g (90% yield).
82%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;	3 20.9 g (73.42 mmol) of Compound A, 30 g (80.76 mmol) of intermediate M-3, and 10.58 g (110.13 mmol) of sodium terbutyrate were placed in a round bottom flask and added thereto. 700 ml of toluene was allowed to dissolve. Subsequently, 0.67 g (0.734 mmol) of Pd(dba) 2 and 0.45 g (2.20 mmol) of tri-tert-butylphosphine were sequentially added thereto. The mixture was refluxed under a nitrogen atmosphere and stirred for 4 hours. When the reaction was completed, the resultant was extracted with toluene and distilled water, and the organic layer obtained therefrom was dried over magnesium sulfate and filtered, and the filtered solution was concentrated under reduced pressure. Subsequently, the product obtained therefrom was purified by a hexane column chromatography using n-hexane/dichloromethane (8:2 by volume) to obtain 39.4 g of Compound I-57 (yield 82%).

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - KR2016/22081, 2016, A Location in patent: Paragraph 0477; 0478; 0479
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD.; SAMSUNG C&T CORPORATION - TW2016/2060, 2016, A Location in patent: Paragraph 0109

7
[ 897921-59-4 ]
3-(4-bromophenyl)-5-phenyl-10,10-dimethyl-5,10-dihydroindeno[1,2-b]indole [ No CAS ]
(biphenyl-4-yl)-{4-(naphthalen-1-yl)phenyl}-{4-(5-phenyl-10,10-dimethyl-5,10-dihydroindeno[1,2-b]indol-3-yl)phenyl}amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux;	4 (Biphenyl-4-yl) -{4- (naphthalen-1-yl) phenyl}- {4- (5-phenyl-10,10-dimethyl-5,10-dihydroindeno [1,2- b]Indol-3-yl)Phenyl} amine synthesis: In a nitrogen-purged reaction vessel,11.0 g of 3- (4-bromophenyl) -5-phenyl-10,10-dimethyl-5,10-dihydroindeno [1,2- b] indole synthesized in Example 2,(Biphenyl-4-yl) - {4- (naphthalen-1-yl) phenyl} amine10.1 g,0.2 g of palladium acetate,6.8 g of tert-butoxysodium,110 ml of toluene and0.34 g of tri (tert-butyl) phosphine. The mixture was heated and refluxed with stirring for 3 hours. The mixture was cooled to room temperature and added to 1000 ml of methanol. The resultant precipitate was collected by filtration, dissolved in toluene by heating, and insoluble matter was removed by high-temperature filtration. After the filtrate was concentrated, methanol was added, and the precipitated crude product was collected by filtration. The crude product was recrystallized three times with a mixed solvent of THF and acetone and recrystallized with THF to give (biphenyl-4-yl) -{4-(naphthalen-1-yl) phenyl }-{4- (5-phenyl-10,10-dimethyl-5,10-dihydroindeno [1,2- b] indol-Phenyl} amine(Compound 72) (10.7 g, yield 60%) as a white powder.

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR2016/17055, 2016, A Location in patent: Paragraph 0613-0625

8
[ 897921-59-4 ]
[ 1257251-75-4 ]
C₅₃H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene for 8h; Reflux; Inert atmosphere;	5 5. Synthesis of Compound 34 j0078] Intermediate A was synthesized using substantially the same method used for Compound 1. Under an Ar atmosphere, 6.42 g of Compound A, 6.00 g of Compound E, 0.563 g of Pd(dba)2, 0.87 g of(t-Ru)3P, and 4.66 g of sodium t-butoxide were added to a 200 mE 3-neck flask, and the mixture was stirred, heated, and refluxed in 150 mE of toluene for about 8 hours. The reaction was air cooled to room temperature, water was added to separate an organic phase, and the product was isolated by solvent distillation. The resulting crude product was purified using silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), followed by recrystallization from a mixed solvent of toluene/hexane to yield about 9.44 g of Compound 34 (yield: about 85%) as a white solid.10079] The molecular weight of Compound 34 measured through FAR-MS was about 688. The ‘H-NMR (CDC13) chemical shifi value (ö) of Compound 34 was as follows:8.53 (d, 2H, J=7.60 Hz), 8.40 (d, 1H, J=7.80 Hz), 8.05-8.02 (m, 2H), 7.85-7.83 (m, 2H), 7.80 (s, 1H), 7.73-7.51 (m, 11H), 7.40-7.25 (m, 1OH), 7.16-7.09 (m, 3H), 7.07-7.02 (m, 6H).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2016/359113, 2016, A1 Location in patent: Paragraph 0078; 0079

9
[ 897921-59-4 ]
C₂₄H₁₇BrSi [ No CAS ]
C₅₂H₃₇NSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	Synthesis of compound 5 To the reaction vessel was added Compound A (4.00 g, 9.68 mmol),Compound C (3.95 g, 10.64 mmol),Pd (dba) 2 (0.28 g, 0.48 mmol),Sodium t-butoxide (0.93 g, 9.68 mmol) was added and the argon replaced.Next, dehydrated toluene (97 mL) and tri (t-butyl) phosphine toluene solution (1.5 M, 1.29 mL, 1.94 mmol) were added and the mixture was heated and stirred at 80 ° C for 1 hour.After cooling, water was added to the reaction solution to extract an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary rotary evaporator. The resulting crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane) to obtain a solid. The solid was recrystallized from toluene and ethanol to obtain 6.47 g of a white powdery solid represented by the target Compound 5 at a yield of 95%

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - KR2017/100698, 2017, A Location in patent: Paragraph 0162-0164

10
[ 897921-59-4 ]
C₂₆H₁₇Cl [ No CAS ]
C₅₄H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	7 7. Synthesis of Compound 103 Compound F was synthesized by the same synthetic method of Compound F in the synthetic method of Compound 11. Then, under an argon (Ar) atmosphere, 4.20 g of Compound F, 4.70 g of Compound L. 1.11 g of sodium t-butoxide, 331 mg of bis(dibenzylideneacetone)palladium (0) (Pd(dba)2), and 1.53 ml of 1.5 M toluene solution of tri-t-butyl phosphine (93u3P) were added to 150 ml of toluene, and deaerated. The reaction mixture was stirred and refluxed for 24 hours. After that, the reaction product was cooled, extracted with chloroform, and washed with a saturated saline solution.10165] The organic layer thus obtained was dried with anhydrous sodium sulfate, filtered, and concentrated, and residues were separated by column chromatography to obtain 6.93 g (yield 86%) of Compound 103 as a white solid. The molecular weight of the compound measured by FAI3-MS was 699. In addition, the chemical shifi values of the compound measured by ‘H-NMR were 8.89 (d, 2H, J=8 Hz), 8.00 (d, 1H, J=8 Hz), 7.92 (dd, 1H, J=2, 8 Hz), 7.86 (d, 1H, J=8 Hz), 7.78-7.33 (21H), 7.33-7.20 (4H), 7.20-7.03 (6H), 6.99 (ddd, 1H, J=1, 1, 8 Hz). From the results, the white solid compound was identified as Compound 103.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - US2018/114907, 2018, A1 Location in patent: Paragraph 0163; 0164; 0165

11
[ 897921-59-4 ]
[ 371-40-4 ]
C₃₄H₂₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate In N,N-dimethyl-formamide at 170℃; for 15h;	4.4 (4) Synthesis of Intermediate-21 Add 37.1 (100 mmol, 1.0 eq.) to a dry 2L three-necked flask.N-(4-(-1-naphthyl)phenyl)-4-benzidine and 11.1 g (100 mmol, 1.0 eq.) of p-fluoroaniline, followed by addition of dry and degassed 800 ml of DMF as solvent, with mechanical stirring Then, 65.2 g (200 mmol, 2.0 eq.) of cesium carbonate was added slowly. The temperature was raised to 170 ° C and the reaction was allowed to continue for 15 hours. After the reaction was completed, the mixture was cooled to room temperature, stirred with water for 1 hour, solid formed, suction filtered, washed with a small amount of ethanol, and then beat three times with ethanol at room temperature, suction filtration, and dried to give 38 g of intermediate-21 in a yield of 85%.

Reference： [1]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - CN108178765, 2018, A Location in patent: Paragraph 0142; 0155; 0157; 0158

12
[ 897921-59-4 ]
[ 371-40-4 ]
C₅₉H₃₇BrN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 170 °C 2: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine / toluene / 3 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - CN108178765, 2018, A

13
[ 1160294-93-8 ]
[ 13922-41-3 ]
[ 897921-59-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12.0h;Inert atmosphere; Reflux;	31 g (95.62 mmol) of M-2 and 24.7 g (143.43 mmol) of naphthalen-1-ylboronic acid were placed in a round bottom flask, and 400 ml of toluene was added thereto to dissolve it, and it was added thereto. A 250 ml aqueous solution obtained by dissolving 39.65 g (286.85 mmol) of potassium carbonate was stirred and the mixture was stirred. Subsequently, 2.21 g (1.91 mmol) of tetratriphenylphosphine palladium was added thereto, and the obtained mixture was refluxed under a nitrogen atmosphere and stirred for 12 hours. When the reaction was completed, the resultant was extracted with dichloromethane and distilled water, the extracted solution was dried over magnesium sulfate and filtered, and the filtered solution was concentrated under reduced pressure. Subsequently, the product obtained therefrom was purified by hydrazine column chromatography using n-hexane/dichloromethane (7:3 vol/vol) to obtain 31.3 g of intermediate M-3 (yield 88%).

Reference： [1]Patent: TW2016/2060,2016,A .Location in patent: Paragraph 0093

14
[ 32228-99-2 ]
[ 897921-59-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 12 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD.; SAMSUNG C&T CORPORATION - TW2016/2060, 2016, A

15
[ 897921-59-4 ]
C₂₂H₂₃Br [ No CAS ]
C₅₀H₄₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 110℃; for 5h; Inert atmosphere;	Synthesis of Compound 34 A monoamine compound according to an embodiment, Compound 34, may be synthesized, for example, by the following Reaction 5: According to the process of Reaction 5, Compound 34 was synthesized. Referring to Reaction 5, under an argon (Ar) atmosphere, 3.00 g (8.17 mmol) of Compound J, 3.34 g (8.98 mmol) of Compound K, 0.23 g (0.408 mmol) of Pd(dba)2, 1.30 ml (1.6 M solution, 0.82 mmol) of tri(tert-butylphosphine), and 2.35 g (24.5 mmol) of NaOt-Bu were added, and heated and refluxed in 100 ml of a toluene solvent at about 110° C. for about 5 hours. After cooling in the air, the crude product thus obtained was separated by silica gel chromatography and recrystallized to obtain 3.72 g (6.13 mmol, yield 75%) of a target material, Compound 34. A molecular ion peak of m/z=657.4 was verified by measuring FAB-MS, and from the result, the product was identified as the target material, Compound 34.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2019/165273, 2019, A1 Location in patent: Paragraph 0185; 0186

16
[ 897921-59-4 ]
[ 319906-45-1 ]
C₄₃H₃₂BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.58%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 18℃; for 16h;Inert atmosphere;	2-Bromo-7-iodo-9,9-dimethylhydrazine (10.0 g, 25.06 mmol),N-(4-(-1-naphthyl)phenyl)-4-benzidine (6.39 g, 17.21 mmol),Tris(dibenzylideneacetone)dipalladium (0.15 g, 0.16 mmol),Tri-tert-butylphosphine (0.07 g, 0.33 mmol) and sodium tert-butoxide (2.41 g, 23.5 mmol)Add toluene (100 mL), heat to 18 C under nitrogen, stir for 16 h;After cooling to room temperature, the reaction solution was filtered, and the filtrate was evaporated under reduced pressure;The obtained crude product was purified by silica gel column chromatography using n-heptane as a mobile phase.The crude product is then recrystallized and purified with n-heptane.The pale yellow solid intermediate II-H (3.07 g, 28.58%) was obtained.

Reference： [1]Patent: CN110183333,2019,A .Location in patent: Paragraph 0104; 0110; 0111

17
[ 897921-59-4 ]
C₂₆H₁₇Cl [ No CAS ]
C₅₄H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 5h; Inert atmosphere;	6 (Synthesis of final compound 11) General procedure: Under an argon (Ar) atmosphere,Add to 100ml three-necked flask2.50 g of N-3-dibenzofuranyl-3-dibenzofuranamine, 2.38 g of intermediate compound C,0.10 g of tBu3P and 33 ml of which dissolved 1.36 g tBuONa anhydrous toluene solution,It was then heated and stirred at about 80 ° C for about 5 hours.After cooling in air, dichloromethane was added and the organic layer was separated and collected.The solvent was removed by distillation.The crude product thus obtained was separated by silica gel column chromatography (using toluene and hexane).3.75 g (yield 87%) of compound 11 was obtained as a pale yellow solid.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - CN110003018, 2019, A Location in patent: Paragraph 0194-0197; 0206-0208; 0237; 0242-0244

18
[ 897921-59-4 ]
C₃₀H₂₂BrNSi [ No CAS ]
C₅₈H₄₂N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Reflux; Inert atmosphere;	1 Under an argon atmosphere, the intermediate A-3 (8.02g, 15.9mmol), Pd (dba) 2 (0.27g, 0.03 equivalent, 0.5mmol), NaOtBu (3.05g, 2 equivalent, 31.8mmol), toluene (80mL ), N- (4- (naphthalen-1-yl) phenyl)-[1,1'-biphenyl] -4-amine (6.50g, 1.1 equivalent, 17.5mmol) and tBu3P (0.32g, 0.1 equivalent , 1.6 mmol) was added to a 500 mL three-necked flask in order, and the mixture was stirred and heated to reflux for about 6 hours. After cooling to room temperature in the air, water was added to the reaction solution, and the organic layer was separated and taken out. Toluene was added to the remaining water layer, and then the water layer was extracted to obtain another organic layer. The organic layers were combined and washed with brine, and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (using a mixture of hexane and toluene as a developing solvent) to obtain compound A15 (10.75 g, yield 85%) as a white solid.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN110885342, 2020, A Location in patent: Paragraph 0193; 0207-0211

19
[ 897921-59-4 ]
C₂₀H₁₂ClNO [ No CAS ]
C₄₈H₃₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 120℃; Inert atmosphere;	1.1-3 1-3. Synthesis of Compound A25 Under an argon (Ar) atmosphere, 5.00 g (15.7 mmol) of intermediate IM-2 was added one by one to a 200 ml three-necked flask0.27g (0.03 equivalent, 0.5mmol) of Pd (dba) 2, 3.02g (2.0 equivalent, 31.5mmol) of NaOtBu,78 ml of toluene, 6.43 g (1.1 equivalents, 17.3 mmol) of N- [4- (naphthalen-1-yl) phenyl]-(1,1′-biphenyl) -4-amine and 0.32 g (0.1 equivalents, 1.6mmol) of tBu3P, And then heated to about 120 and stirred. After cooling to room temperature in the air, water was added to the reaction solution, and the organic layer was taken separately.Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layers were put together and washed with saturated saline solution and dried over MgSO4.After filtering MgSO4, the organic layer was concentrated to obtain a crude product.The crude product thus obtained was separated by silica gel column chromatography using a mixture solvent of hexane and toluene as a developing solution,To obtain compound A25 (8.32 g, yield 81%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN111039956, 2020, A Location in patent: Paragraph 0141; 0158-0162

20
[ 897921-59-4 ]
C₂₀H₁₂ClNO [ No CAS ]
C₄₈H₃₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere;	1.1-5 Synthesis of Compound A50 Under an argon (Ar) atmosphere, 5.00 g (15.7 mmol) of intermediate IM-6 was added to a 200 ml three-necked flask one by one0.27g (0.03 equivalent, 0.5mmol) of Pd (dba) 2, 3.02g (2.0 equivalent, 31.5mmol) of NaOtBu, 78ml of toluene,6.43g (1.1 equivalents, 17.3mmol) of N- [4- (naphthalen-1-yl) phenyl]-(1,1'-biphenyl) -4-amine and 0.32g (0.1 equivalents, 1.6mmol) of tBu3P,Then heat to about 120 ° C and stir. After cooling to room temperature in the air, water was added to the reaction solution, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layers were put together and washed with brine solution and dried over MgSO4. After filtering MgSO4, the organic layer was concentrated.The crude product thus obtained was separated by silica gel column chromatography using a mixture solvent of hexane and toluene as a developing solution to obtain compound A50 (7.60 g, yield 74%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN111039956, 2020, A Location in patent: Paragraph 0141; 0173-0176; 0181-0182

21
[ 897921-59-4 ]
C₂₀H₁₂ClNS [ No CAS ]
C₄₈H₃₂N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 120℃; Inert atmosphere;	1.1-13 Synthesis of Compound B100 Under an argon (Ar) atmosphere, to a 200ml three-necked flask were added 5.00g (15.0mmol) of intermediate IM-22,0.26 g (0.03 equivalent, 0.4 mmol) of Pd (dba) 2, 2.88 g (2.0 equivalent, 30.0 mmol) of NaOtBu,75ml of toluene, 6.12g (1.1 equivalent, 16.5mmol) ofN- [4- (naphthalen-1-yl) phenyl]-(1,1’-biphenyl) -4-amine and 0.30 g (0.1 equivalent, 1.5 mmol) of tBu3P,Then heat to about 120 ° C and stir. After cooling to room temperature in the air, water was added to the reaction solution, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layers were put together and washed with brine solution and dried over MgSO4. After filtering MgSO4, the organic layer was concentrated. The crude product thus obtained was separated by silica gel column chromatography using a mixture solvent of hexane and toluene as a developing solution to obtain compound B100 (8.01 g, yield 80%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN111039956, 2020, A Location in patent: Paragraph 0141; 0254-0257; 0262-0263

22
[ 897921-59-4 ]
C₂₂H₁₃BrO [ No CAS ]
C₅₀H₃₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.34%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 5h; Inert atmosphere;	1.3 (3) Synthesis of compound 1: Intermediate 2 (12.00g, 32.15mmol) and raw material D-1 (11.94g, 32.15mmol) were dissolved in 40.00ml of toluene solution, followed by air exchange 3 times, adding tris(dibenzylideneacetone) under nitrogen protection Palladium (0.30g, 0.32mmol),Tri-tert-butyl phosphine (0.33g, 1.61mmol) and sodium tert-butoxide (6.18g, 64.3mmol), stir well, heat up to 90°C, and reflux for 5h; after the reaction is over, lower the temperature slightly,Use diatomaceous earth to filter to remove salts and catalysts,After the filtrate is cooled to room temperature, it is washed three times with water to retain the organic phase.Then the aqueous phase was extracted with ethyl acetate; after combining the organic phases,Anhydrous magnesium sulfate was used for drying, and a rotary evaporator was used to remove the solvent; using a mixed solution of dichloromethane and petroleum ether (V:V=10:4), the remaining substance was purified by column chromatography to obtain compound 1 (17.78g) , Yield: 83.34%,

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN112079802, 2020, A Location in patent: Paragraph 0069; 0074-0081

23
[ 897921-59-4 ]
C₂₀H₁₂ClNO [ No CAS ]
C₄₈H₃₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux;	1-2 Synthesis of Compound 15 Under an argon atmosphere, to a 300 ml, three-neck flask, Intermediate A-4 (4.8 g, 14.98 mmol), Pd(dba)2 (0.43 g, 0.05 eq, 0.75 mmol), NaOtBu (1.44 g, 1 eq, 14.98 mmol), toluene (164 ml), N,N-(4-biphenyl)-[4-(1-naphthalenyl)phenyl]yl)amine (6.12 g, 1.1 eq, 16.48 mmol) and tBu3P (0.61 g, 0.2 eq, 3.0 mmol) were added in order, followed by heating, refluxing and stirring for about 6 hours. After cooling to room temperature in the air, water was added to a reaction solvent, and the organic layer was separated. The aqueous layer was extracted with toluene. The combined organic layers were collected and then washed with a saline solution and dried with MgSO4. MgSO4 was filtered and removed, and the filtrate was concentrated to obtain a crude product. The crude product was separated by silica gel column chromatography to obtain Intermediate A15 (6.8 g, yield 70%) as a white solid.The molecular ion peak (m/z) of Intermediate A15 measured by a FAB-MS measurement method was 652.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2021/104675, 2021, A1 Location in patent: Paragraph 0137-0139

24
[ 897921-59-4 ]
[ 37842-69-6 ]
C₄₈H₃₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis(tri-tertiary-butylphosphine)palladium⁽⁰⁾; sodium tertiary butoxide In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Inert atmosphere; Heating;	1 Preparation Example 1 Compound A (10 g, 34. 63 mmol) and compound a (13.12 g, 35.32 mmol) were completely dissolved in 220 mL of Xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (4.65 g, 48.48 mmol) was added, and Bis(tri-tert-butylphosphine)palladium(0)(BTP)(0.09g, 0.17mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 240 mL to prepare Compound 1 (17.49 g, yield: 81%).
51%	With bis(tri-tertiary-butylphosphine)palladium⁽⁰⁾; sodium tertiary butoxide for 2h; Inert atmosphere; Reflux;	2-2 Preparation Example 2-2 Compound subA-1 (10 g, 34.6 mmol), Compound sub2 (12.9 g, 34.6 mmol) and sodium tert-butoxide (6.7 g, 69.3 mmol) were added to xylene (200 ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added thereto, When the reaction was completed after 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give Compound 2-2 (11 g). (Yield: 51%, MS: [M+H]+=624)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/75623, 2021, A Location in patent: Paragraph 0191-0194
[2]Current Patent Assignee: LG CHEM CO.,LTD. - US2022/85300, 2022, A1 Location in patent: Paragraph 0197-0198

25
[ 897921-59-4 ]
[ 244205-40-1 ]
C₃₄H₂₆BNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium <i>tert</i>-butylate; triphenylphosphine In toluene for 12h; Inert atmosphere; Reflux;	1 In a three-necked flask, add 0.01mol of raw material B-1, 0.012mol of raw material A-1, 0.03mol potassium tert-butoxide, 1x10-4mol Pd2(dba)3, under a nitrogen atmosphere, 1x10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours. The sampling point board shows that there is no remaining raw material B-1, and the reaction is complete; natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain intermediate F-1.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN113416164, 2021, A Location in patent: Paragraph 0296-0298

26
[ 897921-59-4 ]
C₄₀H₂₇BrClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine / toluene / 12 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water / 24 h / 105 °C / Inert atmosphere