66217-56-9|4,4,5,5-Tetramethyl-2-octyl-1,3,2-dioxaborolane| Ambeed

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Quality Control of [ 66217-56-9 ] Purity: 98% SDS Specification

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Product Details of [ 66217-56-9 ]

CAS No. :	66217-56-9
Formula :	C₁₄H₂₉BO₂
M.W :	240.19
SMILES Code :	CCCCCCCCB1OC(C)(C)C(C)(C)O1
InChI Key :	JYYHTFAJEPMWME-UHFFFAOYSA-N
Pubchem ID :	11253440

Safety of [ 66217-56-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 66217-56-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 66217-56-9 ]

[ 66217-56-9 ] Synthesis Path-Downstream 1~35

1
[ 591-50-4 ]
[ 66217-56-9 ]
[ 2189-60-8 ]

References: [1]Chemistry Letters,1989,p. 1405 - 1408.
[2]Chemistry Letters,1989,p. 1405 - 1408.
[3]Chemistry Letters,1989,p. 1405 - 1408.

2
[ 111-65-9 ]
[ 73183-34-3 ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 16439 - 16443.
[3]Chemical Communications,2001,p. 619 - 620.
[4]Chemical Communications,2001,p. 619 - 620.
[5]Chemical Communications,2001,p. 619 - 620.
[6]Chemical Communications,2001,p. 619 - 620.
[7]Organometallics,2013,vol. 32,p. 6170 - 6173.
[8]Chemical Communications,2018,vol. 54,p. 8202 - 8205.
[9]Journal of the American Chemical Society,2020,vol. 142,p. 6488 - 6492.

3
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[ 77117-48-7 ]
[ 73183-34-3 ]
[ 66217-56-9 ]
2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 15334 - 15335.
[2]Journal of the American Chemical Society,2004,vol. 126,p. 15334 - 15335.

4
[ 14850-23-8 ]
[ 25015-63-8 ]
[ 66217-56-9 ]

Yield	Reaction Conditions	Operation in experiment
> 95%	With C39H42CoN2PSi; In Cyclooctan; at 23℃; for 0.5h;	10142] A scintillation vial was charged with 0.100 g (0.78 mmol, 1 equivalent) of pinacol borane (HBPin), 0.088 g (0.78 mmol, 1 equivalent) of trans-4-octene, 0.088 g (0.78 mmol, 1 equivalent) of cyclooctane, and 0.04 mmol, 0.05 equivalent) of the cobalt complex. The vial was then capped and its contents were stirred at 23 C. The reaction mixture was quenched by exposing the mixture to air, and the solvent removed in vacuo. The resulting residue was purified by extraction into hexane and passage through a silicaplug. The isolated compound was analyzed by H and ‘ C NMR spectroscopy. The hydroborations were performed according to this procedure to determine the time required to achieve at least 70% conversion of the trans-4-octene to the terminal octyl pinacolborane. The information for the hydroborations for the four cobalt complexes is provided in Table 10.
	With C33H58CoN3PSi2; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cis-Octene and Trans-Octene hydroborationCis-Octene and Trans-Octene Hydroboration (0228) The hydroboration of cis-4-octene or trans-4-octene using the compositions and methods disclosed herein was also investigated. Specifically cis-4-octene or trans-4-octene was contacted with pinacolborane and 0.1 to 1.0 mol % of the N2-phosphinyl amidine complex of Structure PAMC1 or Structure PAMC2. The reaction was carried out in the absence of solvent and 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, depicted as Structure ABP2, was synthesized according to GP2. After drying in vacuo the alkyl product was isolated as a colorless oil. Data obtained from 13C DEPT-Q NMR experiments confirmed the formation of the terminal hydroboration product. The reaction progress was followed by the use of NMR and the results of the hydroboration reaction are presented in Table 6. The results demonstrate that less than 5% of the cis-4-octene was observed to convert to 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane when using up to 1.0 mol. % of the N2-phosphinyl amidine complex of Structure PAMC2 as the reaction catalyst in contrast to a conversion of greater than 95% observed when using 1.0 mol. % of the N2-phosphinyl amidine complex of Structure PAMC1. However, when using the following amounts of alkene substrate and catalyst: cis-4-octene (160 μL, 1 mmol), PMAC2 (0.0016 g, 2.5 mol %), the 1H and 11B NMR spectra obtained indicated full conversion of the starting materials. (0231) The results were similar when using trans-4-octene as the substrate. For example, when using trans-4-octene (160 μL, 1 mmol) and PMAC1 (0.016 g, 2.5 mol %) according to GP1, the 1H and 11B NMR spectra obtained indicated full conversion of the starting materials. In contrast, when using trans-4-octene (160 μL, 1 mmol) and PMAC2 (0.032 g, 5 mol %) according to GP1, the 1H and 11B NMR spectra obtained indicated a small amount of the starting materials were converted. General Procedure for Determination of Conversion of Catalytic Alkene Hydroboration (GP1). (0215) In a nitrogen atmosphere glovebox, an oven-dried screw-capped vial containing a stirbar was charged with the desired quantity of pinacolborane and the desired quantity of the desired alkene. The desired quantity of the desired catalyst was then added as a solid and the vial was sealed with a cap containing a PTFE septum and stirred in the glovebox for 1 hour. After 1 hour the vial was removed from the glovebox and the catalyst mixture was deactivated by exposure to air. The contents of the vial were extracted with CDCl3 and filtered through silica into a NMR tube. The 1H and/or 11B NMR spectra were analyzed to monitor the progress of the reaction. If no pinacolborane or alkene/carbonyl compound was found to be present in the sample, the reaction was determined to have achieved full conversion. For 4-octene isomers, the 13C DEPT-Q NMR spectrum was also analyzed to aid in determining if an isomerization process involving the starting alkene had occurred.

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 13918 - 13922.
[2]Patent: US2018/44354,2018,A1 .Location in patent: Paragraph 0140; 0141; 0142; 0143; 0144.
[3]Chemical Communications,2014,vol. 50,p. 11056 - 11059.
[4]Journal of the American Chemical Society,1996,vol. 118,p. 909 - 910.
[5]ACS Catalysis,2015,vol. 5,p. 622 - 626.
[6]Tetrahedron,2004,vol. 60,p. 10695 - 10700.
[7]Tetrahedron Letters,2006,vol. 47,p. 1299 - 1302.
[8]Journal of the American Chemical Society,1996,vol. 118,p. 909 - 910.
[9]Journal of the American Chemical Society,2013,vol. 135,p. 19107 - 19110.
[10]Patent: US9120826,2015,B1 .Location in patent: Page/Page column 111; 113; 114.
[11]Organometallics,2017,vol. 36,p. 417 - 423.
[12]ACS Catalysis,2018,vol. 8,p. 9907 - 9925.

5
[ 111-66-0 ]
[ 25015-63-8 ]
[ 66217-56-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium triethylborohydride; at 23℃; for 3h;Inert atmosphere;Catalytic behavior;	MOF-Co catalysts are also active in hydroborylation of alkenes or dehydrogenative C-H borylation of arenes to afford alkyl or arylboronates, which are versatile reagents in organic synthesis. Alkene hydroboration reactions were performed with 0.1-0.01 mol % MOF-Co in a neat, 1:1.2 equiv mixtures of alkene and pinacolborane (HBpin) at room temperature to obtain the highest yields (Table 11). At a 0.1 mol % Co loading, bpyv-MOF-Co gave complete conversion of 1-octene within 16 h at room temperature to furnish a mixture of 66% anti-Markovnikov octylboronate ester and 34% internal alkenes. However, under identical reaction conditions, mPT-MOF-Co afforded exclusively octylboronate ester in 97% yield with TON up to 10,000 (Table 11). The hydroboration of other terminal alkenes such as 1-decene, 5-methyl-1-hexene and 6-chloro-1-hexene occurred selectively in anti-Markovnikov fashion to afford corresponding alkylboronates in excellent yields with 0.1-0.01 mol % mPT-MOF-Co. mPT-MOF-Co was also active in catalytic hydroboration of internal alkenes. Importantly, mPT-MOF-Co can be recycled at least 15 times without any noticeable diminishing activity in hydroboration of 1-octene. A negligible leaching of Co (<0.01%) and Zr (<0.005%) was observed into the supernatant after run 1. No hydroboration reaction was observed after removal of mPT-MOF-Co from the reaction mixture, which rules out any role of leached cobalt species in catalyzing hydroboration. Additionally, Co-nanoparticles or homogeneous controls, Me2bpy-Co and PT-Co, are barely active in catalyzing hydroboration reactions (e.g., entry 1, Table 11). The higher activities of MOF-Co catalysts strongly support the beneficial effect of active site isolation in the MOF frameworks, which prevents any intermolecular deactivation. (0238) [table-us-00011-en] TABLE 11 MOF-Co-Catalyzed Hydroboration of Alkenesa Co-catalysts % Yield Entry Substrate Product (mol % loading) Time (TONs) 1-octene bpyv-MOF-Co (0.1) mPT-MOF-Co (0.1) mPT-MOF-Co (0.01) 16 h 16 h 3 h 66 (660) 100 (>1000) 100 (10000) CoCl2 (0.1) 20 h 0 Co(Me2bpy)Cl2 (0.1) 20 h 37 1-decene mPT-MOF-Co (0.1) 16 h 100 (>1000) mPT-MOF-Co (0.1) mPT-MOF-Co (0.01) 16 h 4 d 100 (>1000) 100 (10000) mPT-MOF-Co (0.1) 2 d 86 mPT-MOF-Co (0.1) 18 h 100 (>1000) mPT-MOF-Co (0.1) (0240) RRN 78Inspired by the high activity of mPT-MOF-Co in alkene hydroboration, the catalytic activity of MOF-Co catalysts in dehydrogenative borylation of aromatic C-H bonds were investigated. In homogeneous catalysis, although a number of nitrogen and phosphine-based iridium(I) catalysts have been reported, the bipyridyl- or phenanthryl-derived iridium catalysts are the most active and widely used in C-H borylation. Efforts in developing heterogeneous borylation catalysts has been made based on precious metals such as iridium(0) nanoparticles, insoluble iridium complex, or silica-supported rhodium and iridium catalysts. Recently, bis(imino)pyridine- and bis(phosphino)pyridine-supported cobalt catalysts have been reported for arene C-H borylation. mPT-MOF-Co was initially employed in C-H borylation reactions for optimized conditions such as temperature, activating and borylating reagents, solvents, and in neat arenes (without using a solvent) to obtain the best results. The screening experiments revealed that the highest yields were obtained when the borylation reactions were performed in neat arene at 100 C. or refluxed in n-heptane at 100 C. for solid substrates. mPT-MOF-Co catalyzed borylation of o- and m-xylene occurred selectively at the least sterically hindered C-H bonds. 1,2-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-m-xylene were obtained from o- and m-xylene in 90 and 92% yield, respectively, with 0.1 mol % mPT-MOF-Co (e.g., entries 1 and 2, Table 12). Although only phenylboronate was afforded from benzene as a monoborylated product, the borylation of toluene furnished a mixture of meta- and para-substituted products in a 60:40 ratio. Interestingly, both mPT-MOF-Co is significantly more active in C-H borylation of arenes than their homogeneous control PT-Co. 1.0 mol % of PT-Co afforded 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-m-xylene from m-xylene in only 8% conversion in four days, after which no further conversion was observed with further heating. In contrast, the conversion of m-xylene proceeded with time until completion in the presence of 0.1 mol % mPT-MOF-Co (FIG. 5). This result indicates that mPT-MOF-Ir is at least 125 times more active than the homogeneous control for the C-H borylation reaction. (0241) [table-us-00012-en]
99%	With calcium chloride; In chloroform-d1; at 110℃; for 6h;Glovebox;	In the glove box, 3mol% calcium chloride, 0.2 mmol 1-octene, 0.4 mmol pinacol borane, and 50 μl CDCl were sequentially added to the reaction flask, and then removed from the glove box, stirred at 110 C. for 6 h to obtain 47.5 mg The product was obtained in 99% yield by NMR spectroscopy.
75%	With borane-THF; In tetrahydrofuran; at 60℃; for 18h;Inert atmosphere;	General procedure: Phenylacetylene (1.00 mmol, 0.110 mL), pinacolborane (1.10 mmol, 0.160 mL) and H3B·THF (0.100 mmol, 1 M, 0.100 mL) were added sequentiallyto a sealed reaction vial flushed with an nitrogen atmosphere. The reaction mixture was stirred for 1 h at 60 C. The reaction was then quenched by filtration through a short silica plug (5 cm) with CH2Cl2. The solvents were removed under reduced pressure and the residue was purified by flash column chromatography (SiO2; hexane/EtOAc, 98:2), to give the boronic ester 2a (215.1 mg, 0.93 mmol, 93%) as a colourless oil.

	With C33H58FeN3PSi2; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Octene hydroboration The hydroboration of 1-octene using the compositions and methods disclosed herein was also investigated. Specifically 1-octene was contacted with pinacolborane and 0.1 to 1.0 mol % of the N2-phosphinyl amidine complex of Structure PAMC1 or Structure PAMC2. The reaction was carried out in the absence of solvent. Specifically, 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, depicted as Structure ABP2, was synthesized according to GP2 and after drying in vacuo the product was isolated as a colorless oil. The reaction progress was followed by the use of NMR and the results of the hydroboration reaction are presented in Table 5. NMR characterization of the alkylboron product resulted in the following: 1H NMR (300.1 MHz, CDCl3): δ 1.35 (m, 2H), 1.18-1.22 (overlapping peaks, 22H), 0.83 (m, 3H), 0.72 (t, 2H, J=8 Hz). 13C{1H}NMR (75.5 MHz, CDCl3): δ 83.0, 32.6, 32.1, 29.5-29.6 (overlapping peaks), 25.0, 24.2, 22.9, 14.3. 11B NMR (96.3 MHz, CDCl3): δ 34.1. Spectral data are in close agreement with previously reported 1H and 13C NMR characterization data for of 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. General Procedure for Isolation of Alkene Hydroboration Products (Solvent Free) (GP2) (0216) In a nitrogen atmosphere glovebox, an oven-dried screw-capped vial containing a stirbar was charged with the desired quantity of pinacolborane and the desired quantity of the desired alkene. The desired quantity of the desired catalyst was then added as a solid and the vial was sealed with a cap containing a PTFE septum and stirred in the glovebox for 1 hour. After 1 hour the vial was removed from the glovebox and the catalyst mixture was deactivated by exposure to air. The contents were extracted with Et2O (3×2 mL) and the ether extracts were subsequently filtered through silica. The eluent was collected and concentrated under reduced pressure to furnish the hydroboration product. The 1H and 13C NMR spectra of the isolated material were analyzed to determine the purity of the sample.
	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; diphenyl(methyl)phosphine; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Sealed tube;	General procedure: In an Ar-filled glove box, [Ir(COD)Cl]2(1.5%) and diphenylphosphinomethane (3%), and a magnetic stir bar were added to a round bottomflask. The flask was sealed with a rubber septa and removed from the glove box. Under N2, CH2Cl2(0.3 M), pinacolborane (1.2 equiv), and alkene (1.0 equiv) were added successively. The reactionwas sealed and stirred at room temperature for 16 h. The reaction was quenched with methanoland water. The layers were separated and the aqueous layer was extracted with diethyl ether (3x).The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressureto afford the crude product which was purified by silica gel chromatography.
115 mg	With [(tBuPNN)FeCl2]; sodium t-butanolate; In diethyl ether; at 20℃; for 0.5h;Glovebox;	B2pin2 (0.25 mmol, 64 mg), (tBuPNN)FeCl2 (0.0025 mmol, 1.1 mg), and NaOtBu (0.005 mmol, 0.4 mg)were dissolved in Et2O (0.25 mL) in an autoclave. The vessel was purged with H2 then pressurised withH2 (10 bar). This was left to stir for 2 hours, then the pressure was released and the vessel transferredinto a glovebox. 1-Octene (0.50 mmol, 69 μL) was added, and the reaction left to stir for 30 mins. Thesolvent was removed in vacuo and the residue purified by flash column chromatography on silica(40/60 petroleum ether:diethyl ether, 100:0 to 100:20). Volatiles were removed in vacuo to give theprimary boronic ester (115 mg, 96%) as a colourless oil.

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[6]Patent: CN113880873,2022,A .Location in patent: Paragraph 0120-0125.
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[8]Angewandte Chemie - International Edition,2019,vol. 58,p. 592 - 595.
    Angew. Chem.,2019,vol. 131,p. 602 - 605,4.
[9]Chemistry - A European Journal,2014,vol. 20,p. 13918 - 13922.
[10]Organometallics,2018,vol. 37,p. 1462 - 1467.
[11]Organic Letters,2019,vol. 21,p. 4035 - 4038.
[12]Angewandte Chemie - International Edition,2018,vol. 57,p. 10620 - 10624.
    Angew. Chem.,2018,vol. 130,p. 10780 - 10784,5.
[13]Angewandte Chemie - International Edition,2020,vol. 59,p. 13859 - 13864.
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[14]Organic Letters,2021,vol. 23,p. 1681 - 1686.
[15]ACS Catalysis,2019,vol. 9,p. 4025 - 4029.
[16]ACS Catalysis,2015,vol. 5,p. 411 - 415.
[17]New Journal of Chemistry,2019,vol. 43,p. 10531 - 10536.
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[21]Organic Letters,2018,vol. 20,p. 7840 - 7845.
[22]European Journal of Organic Chemistry,2017,vol. 2017,p. 5814 - 5818.
[23]Journal of the American Chemical Society,1996,vol. 118,p. 909 - 910.
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[30]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2404 - 2409.
[31]Advanced Synthesis and Catalysis,2005,vol. 347,p. 50 - 54.
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[34]Organometallics,2007,vol. 26,p. 1191 - 1195.
[35]Angewandte Chemie - International Edition,2012,vol. 51,p. 5730 - 5734.
[36]Organometallics,2013,vol. 32,p. 3121 - 3128.
[37]Organic Letters,2013,vol. 15,p. 2680 - 2683.
[38]Journal of the American Chemical Society,2013,vol. 135,p. 19107 - 19110.
[39]ACS Catalysis,2015,vol. 5,p. 622 - 626.
[40]Patent: US9120826,2015,B1 .Location in patent: Page/Page column 111; 112; 113.
[41]Journal of the American Chemical Society,2016,vol. 138,p. 14860 - 14863.
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[47]Inorganic Chemistry,2021,vol. 60,p. 494 - 504.

6
[ 25015-63-8 ]
[ 7642-15-1 ]
[ 66217-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	With C33H58CoN3PSi2; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cis-Octene and Trans-Octene hydroborationCis-Octene and Trans-Octene Hydroboration (0228) The hydroboration of cis-4-octene or trans-4-octene using the compositions and methods disclosed herein was also investigated. Specifically cis-4-octene or trans-4-octene was contacted with pinacolborane and 0.1 to 1.0 mol % of the N2-phosphinyl amidine complex of Structure PAMC1 or Structure PAMC2. The reaction was carried out in the absence of solvent and 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, depicted as Structure ABP2, was synthesized according to GP2. After drying in vacuo the alkyl product was isolated as a colorless oil. Data obtained from 13C DEPT-Q NMR experiments confirmed the formation of the terminal hydroboration product. The reaction progress was followed by the use of NMR and the results of the hydroboration reaction are presented in Table 6. The results demonstrate that less than 5% of the cis-4-octene was observed to convert to 2-oct-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane when using up to 1.0 mol. % of the N2-phosphinyl amidine complex of Structure PAMC2 as the reaction catalyst in contrast to a conversion of greater than 95% observed when using 1.0 mol. % of the N2-phosphinyl amidine complex of Structure PAMC1. However, when using the following amounts of alkene substrate and catalyst: cis-4-octene (160 μL, 1 mmol), PMAC2 (0.0016 g, 2.5 mol %), the 1H and 11B NMR spectra obtained indicated full conversion of the starting materials. (0231) The results were similar when using trans-4-octene as the substrate. For example, when using trans-4-octene (160 μL, 1 mmol) and PMAC1 (0.016 g, 2.5 mol %) according to GP1, the 1H and 11B NMR spectra obtained indicated full conversion of the starting materials. In contrast, when using trans-4-octene (160 μL, 1 mmol) and PMAC2 (0.032 g, 5 mol %) according to GP1, the 1H and 11B NMR spectra obtained indicated a small amount of the starting materials were converted. General Procedure for Isolation of Alkene Hydroboration Products (Solvent Free) (GP2) (0216) In a nitrogen atmosphere glovebox, an oven-dried screw-capped vial containing a stirbar was charged with the desired quantity of pinacolborane and the desired quantity of the desired alkene. The desired quantity of the desired catalyst was then added as a solid and the vial was sealed with a cap containing a PTFE septum and stirred in the glovebox for 1 hour. After 1 hour the vial was removed from the glovebox and the catalyst mixture was deactivated by exposure to air. The contents were extracted with Et2O (3×2 mL) and the ether extracts were subsequently filtered through silica. The eluent was collected and concentrated under reduced pressure to furnish the hydroboration product. The 1H and 13C NMR spectra of the isolated material were analyzed to determine the purity of the sample.

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 13918 - 13922.
[2]Chemical Communications,2014,vol. 50,p. 11056 - 11059.
[3]Tetrahedron,2004,vol. 60,p. 10695 - 10700.
[4]Organic Letters,2013,vol. 15,p. 2680 - 2683.
[5]Journal of the American Chemical Society,2013,vol. 135,p. 19107 - 19110.
[6]Patent: US9120826,2015,B1 .Location in patent: Page/Page column 111; 113; 114.
[7]ACS Catalysis,2018,vol. 8,p. 9907 - 9925.
[8]Organic Letters,2022,vol. 24,p. 1005 - 1010.

7
[ 75-09-2 ]
[ 66217-56-9 ]
2-(1-chlorononyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 13859 - 13864.
Angew. Chem.,2020,vol. 132,p. 13963 - 13968,6.
[2]Advanced Synthesis and Catalysis,2005,vol. 347,p. 50 - 54.

8
[ 111-65-9 ]
trans-Cp^*Rh(H)2(Bpin)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

9
[ 111-66-0 ]
[ 25015-63-8 ]
[ 26621-57-8 ]
[ 66217-56-9 ]

References: [1]European Journal of Organic Chemistry,2006,p. 4898 - 4904.

10
[ 111-65-9 ]
[ 73183-34-3 ]
[ 66217-56-9 ]
[ 25015-63-8 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 12422 - 12425.
[2]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[3]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[4]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[5]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[6]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[7]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.
[8]Journal of the American Chemical Society,2006,vol. 128,p. 13684 - 13685.

11
[ 111-65-9 ]
(C₅(CH₃)5)IrH₃BO₂C₂(CH₃)4 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 8422 - 8423.

12
[ 111-65-9 ]
(C₅(CH₃)5)IrH₂(BO₂C₂(CH₃)4)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 8422 - 8423.

13
B₂((OC(C⁽²⁾H₃)2)2)2 [ No CAS ]
[ 111-65-9 ]
trans-(pentamethylcyclopentadienyl)Rh(H)2(pinacolboryl)2 [ No CAS ]
C₈H₁₇B(OC(C⁽²⁾H₃)2)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

14
[ 111-65-9 ]
trans-(pentamethylcyclopentadienyl)Rh(H)2(pinacolboryl)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

15
B₂((OC(C⁽²⁾H₃)2)2)2 [ No CAS ]
[ 111-65-9 ]
(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3 [ No CAS ]
C₈H₁₇B(OC(C⁽²⁾H₃)2)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

16
[ 111-65-9 ]
(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3 [ No CAS ]
trans-(pentamethylcyclopentadienyl)Rh(H)2(pinacolboryl)2 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

17
[ 111-65-9 ]
(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3 [ No CAS ]
[ 66217-56-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2538 - 2552.

18
[ 14850-23-8 ]
[ 25015-63-8 ]
[ 358376-08-6 ]
[ 177949-99-4 ]
[ 66217-56-9 ]
[ 1203488-26-9 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[3]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[4]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[5]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[6]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[7]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[8]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[9]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[10]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[11]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[12]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[13]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[14]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[15]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[16]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[17]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[18]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[19]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[20]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[21]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.
[22]Journal of the American Chemical Society,2010,vol. 132,p. 131 - 137.

19
[ 111-83-1 ]
[ 25015-63-8 ]
[ 66217-56-9 ]

Yield	Reaction Conditions	Operation in experiment
93%		bis(cyclopentadiene) titanium dichloride (denoted as Cp2TiCl2, 0.02mmol,5mg), lithium methoxide (denoted as MeOLi, 0.2mmol, 7.6mg), methyl tert-butyl ether (1mL) and Pinacol borane (denoted as HBpin, 0.4mmol,58μL) was sequentially added to a 38mL pressure tube, stirred for 30min and then added 1-bromooctane (denoted as 1a, 0.2mmol, 34μL), under nitrogen (1atm) atmosphere Stir at 90C for 8 hours to obtain a product system containing the structure compound represented by formula 2a. The temperament analysis yield was 93%.

References: [1]Patent: CN112645971,2021,A .Location in patent: Paragraph 0031-0111.
[2]Organometallics,2021,vol. 40,p. 2204 - 2208.
[3]Angewandte Chemie - International Edition,2021,vol. 60,p. 12298 - 12303.
Angew. Chem.,2021,vol. 133,p. 12406 - 12411,6.
[4]Journal of Organic Chemistry,2011,vol. 76,p. 9602 - 9610.

20
[ 104-53-0 ]
[ 66217-56-9 ]
[ 39728-27-3 ]