Name: 18666-68-7|Triphenylvinylsilane|95%
Brand: Ambeed
SKU: A164382
Price: 6.0 USD
Availability: InStock
Rating: 98 (28 reviews)

1
[ 76-86-8 ]
[ 3536-96-7 ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Lühning, Lars H.; Rosien, Michael; Doye, Sven [Synlett, 2017, vol. 28, # 18, p. 2489 - 2494]
[2]Rosenberg et al. [Journal of Organic Chemistry, 1957, vol. 22, p. 1200]

2
[ 75-94-5 ]
[ 591-51-5 ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	In not given at -40°C;;
60%	In not given at -40°C;;
60%	In not given at -40°C;;

Reference： [1]Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]
[2]Nagel; Post [Journal of Organic Chemistry, 1952, vol. 17, p. 1379]
[3][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 26, page 80 - 82]
[4]Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]

3
[ 591-51-5 ]
[ 18666-68-7 ]
[ 18849-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Et₂O, (ii) H₂O; Multistep reaction;
	In not given
	In not given

Reference： [1]Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]
[2]Brook,A.G. et al. [Canadian Journal of Chemistry, 1970, vol. 48, p. 561 - 569]
[3]Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]
[4][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 26, page 80 - 82]

4
[ 108-98-5 ]
[ 18666-68-7 ]
[ 18849-21-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	In neat (no solvent) (C6H5)3SiCHCH2 and thiophenol at 110-160°C;; recrystn. from alc.;;
65%	In acetic acid (C6H5)3SiCHCH2 and thiophenol in glacial acetic acid at 110-160°C;; recrystn. from alc.;;
	With dibenzoyl peroxide

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[2]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[3]Gilman et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 3757]

5
[ 106-45-6 ]
[ 18666-68-7 ]
[ 18870-34-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	In neat (no solvent) (C6H5)3SiCHCH2 and C6H4(CH3)SH at 110-160°C;; recrystn. from alc.;;
57%	In acetic acid (C6H5)3SiCHCH2 and C6H4(CH3)SH in glacial acetic acid at 110-160°C;; recrystn. from alc.;;
	With dibenzoyl peroxide

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[2]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[3]Gilman et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 3757]

6
[ 100-53-8 ]
[ 18666-68-7 ]
[ 18870-33-2 ]

Yield	Reaction Conditions	Operation in experiment
18%	In neat (no solvent) (C6H5)3SiCHCH2 and C6H5CH2SH in glacial acetic acid at 110-160°C;; recrystn. from alc.;;
18%	In acetic acid (C6H5)3SiCHCH2 and C6H5CH2SH in glacial acetic acid at 110-160°C;; recrystn. from alc.;;
	With dibenzoyl peroxide

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[2]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]
[3]Gilman et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 3757]

7
[ 892-20-6 ]
[ 18666-68-7 ]
[ 18822-03-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	80 °C, 4.5 h;;
54%	80 °C, 4.5 h;;
	In not given

Reference： [1]Henry, M. C.; Noltes, J. G. [Journal of the American Chemical Society, 1960, vol. 82, p. 558 - 561]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.15.2, page 359 - 384]
[3]Henry et al. [Journal of the American Chemical Society, 1960, vol. 82, p. 555,556]
[4]Henry, M. C.; Noltes, J. G. [Journal of the American Chemical Society, 1960, vol. 82, p. 558 - 561]
[5][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.4, 1.2.1.1.7.4.2, page 73 - 77]

8
[ 109-99-9 ]
[ 18666-68-7 ]
[ 130752-78-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With di-tert-butyl peroxide at 190℃; for 2h;

Reference： [1]Gevorgyan, Vladimir; Priede, Einars; Liepins, Edvards; Gavars, Maris; Lukevics, Edmunds [Journal of Organometallic Chemistry, 1990, vol. 393, # 3, p. 333 - 338]

9
[ 108-98-5 ]
[ 18666-68-7 ]
[ 66303-55-7 ]
[ 123541-68-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 52% 2: 42%	With oxygen In acetic acid for 21h; Ambient temperature;
1: 52% 2: 42%	With oxygen In acetic acid for 21h; Ambient temperature;

Reference： [1]Yoshida; Nakatani; Isoe [Journal of Organic Chemistry, 1989, vol. 54, # 24, p. 5655 - 5657]
[2]Nakatani, Shogo; Yoshida, Jun-Ichi; Isoe, Sachihiko [Tetrahedron, 1993, vol. 49, # 10, p. 2011 - 2024]

10
[ 100-10-7 ]
[ 18666-68-7 ]
1-(4-Dimethylamino-phenyl)-3-triphenylsilanyl-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone at 35℃;

Reference： [1]Lenges; Brookhart [Journal of the American Chemical Society, 1997, vol. 119, # 13, p. 3165 - 3166]

11
[ 590-86-3 ]
[ 18666-68-7 ]
5-Methyl-1-triphenylsilanyl-hexan-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [Cp*Co(vinyltrimethylsilane)₂_] In acetone at 35℃;

Reference： [1]Lenges, Christian P.; White, Peter S.; Brookhart, Maurice [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6965 - 6979]

12
[ 2043-61-0 ]
[ 18666-68-7 ]
1-Cyclohexyl-3-triphenylsilanyl-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [Cp*Co(vinyltrimethylsilane)₂_] In acetone at 35℃;

Reference： [1]Lenges, Christian P.; White, Peter S.; Brookhart, Maurice [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6965 - 6979]

13
[ 114493-71-9 ]
[ 18666-68-7 ]
1,2-bis[(2E)-2-triphenylsilylethenyl]cyclohexene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With palladium diacetate; silver nitrate; triethylamine In dimethyl sulfoxide for 48h; Ambient temperature;

Reference： [1]Voigt, Katharina; Von Zezschwitz, Paultheo; Rosauer, Keith; Lansky, Annegret; Adams, Amy; Reiser, Oliver; De Meijere, Armin [European Journal of Organic Chemistry, 1998, # 8, p. 1521 - 1534]

14
[ 213340-06-8 ]
[ 18666-68-7 ]
1,2-bis[(2E)-2-triphenylsilylethenyl]cyclopentene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With palladium diacetate; silver nitrate; triethylamine In dimethyl sulfoxide at 100℃; for 48h;

Reference： [1]Voigt, Katharina; Von Zezschwitz, Paultheo; Rosauer, Keith; Lansky, Annegret; Adams, Amy; Reiser, Oliver; De Meijere, Armin [European Journal of Organic Chemistry, 1998, # 8, p. 1521 - 1534]

15
[ 110-91-8 ]
[ 201230-82-2 ]
[ 18666-68-7 ]
4-<3-(triphenylsilyl)-propyl>-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With [Rh(cod)][BPh₄]; hydrogen In toluene at 120℃; for 20h;

Reference： [1]Baerfacker, Lars; Rische, Thorsten; Eilbracht, Peter [Tetrahedron, 1999, vol. 55, # 23, p. 7177 - 7190]

16
[ 18666-68-7 ]
2-Azido-1-bromo-1-triphenylsilylethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With bromine azide In dichloromethane at 20℃; for 7h;

Reference： [1]Bassindale, Alan R.; Kyle, Patricia A.; Soobramanien, Marie-Claire; Taylor, Peter G. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 7, p. 1173 - 1180]

17
[ 56399-99-6 ]
[ 18666-68-7 ]
((1R,2S)-2-Benzyl-cyclopentyl)-triphenyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: (E)-(4-iodobut-1-en-1-yl)benzene With tert.-butyl lithium In diethyl ether; hexane at -78℃; for 0.25h; Stage #2: vinyltriphenylsilane With methanol In diethyl ether; hexane at 20℃; for 0.0833333h;

Reference： [1]Wei, Xudong; Taylor, Richard J. K. [Angewandte Chemie - International Edition in English, 2000, vol. 39, # 2, p. X409-412]

18
[ 18666-68-7 ]
2-deuteroethyltriphenylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With Schwartz's reagent; diclazuril; water-d2 In tetrahydrofuran at 20℃; for 6h;

Reference： [1]Ura, Yasuyuki; Hara, Ryuichiro; Takahashi, Tamotsu [Journal of Organometallic Chemistry, 2000, vol. 611, # 1-2, p. 299 - 303]

19
[ 766-05-2 ]
[ 18666-68-7 ]
1-(2-triphenylsilanyl-ethyl)-cyclohexanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 25℃; for 12h;

Reference： [1]Bunlaksananusorn; Rodriguez; Knochel [Chemical Communications, 2001, # 8, p. 745 - 746]

20
[ 769-68-6 ]
[ 18666-68-7 ]
2-ethyl-2-phenyl-4-triphenylsilanyl-butyronitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 40℃; for 12h;

Reference： [1]Bunlaksananusorn; Rodriguez; Knochel [Chemical Communications, 2001, # 8, p. 745 - 746]

21
[ 829-85-6 ]
[ 18666-68-7 ]
[ 76734-21-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 40℃;

Reference： [1]Bunlaksananusorn, Tanasri; Knochel, Paul [Tetrahedron Letters, 2002, vol. 43, # 33, p. 5817 - 5819]

22
[ 75-77-4 ]
4,4-dimethyl-1-[(dichlorobutyl)stannyl]-3-pentanone [ No CAS ]
[ 18666-68-7 ]
(Z)-2,2-dimethyl-3-(trimethylsiloxy)-7-(trimethylsilyl)-7-(triphenylsilyl)-3-heptene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 4,4-dimethyl-1-[(dichlorobutyl)stannyl]-3-pentanone With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: vinyltriphenylsilane In tetrahydrofuran; hexane at 0℃; for 1h; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; hexane at 0℃; for 0.5h;

Reference： [1]Yamato, Shin-Ya; Yamamura, Go-Hei; Komatsu, Mitsuo; Arai, Masashi; Fukuyama, Takahide; Ryu, Ilhyong [Organic Letters, 2005, vol. 7, # 12, p. 2489 - 2491]

23
[ 18666-55-2 ]
[ 1663-39-4 ]
1,1-dimethylethyl 5-hydroxy-4-(triphenylsilyl)pentanoate [ No CAS ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 50% 2: 14%	With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Puljic, Nicolas; Albert, Matthias; Dhimane, Anne-Lise; Fensterbank, Louis; Lacote, Emmanuel; Malacria, Max [Helvetica Chimica Acta, 2006, vol. 89, # 10, p. 2297 - 2305]

24
[ 18666-55-2 ]
[ 107-13-1 ]
5-hydroxy-4-(triphenylsilyl)pentanenitrile [ No CAS ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 64% 2: 14%	With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Puljic, Nicolas; Albert, Matthias; Dhimane, Anne-Lise; Fensterbank, Louis; Lacote, Emmanuel; Malacria, Max [Helvetica Chimica Acta, 2006, vol. 89, # 10, p. 2297 - 2305]

25
[ 18666-55-2 ]
[ 292638-85-8 ]
tetrahydro-5-(triphenylsilyl)-2H-pyran-2-one [ No CAS ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 20%	With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Puljic, Nicolas; Albert, Matthias; Dhimane, Anne-Lise; Fensterbank, Louis; Lacote, Emmanuel; Malacria, Max [Helvetica Chimica Acta, 2006, vol. 89, # 10, p. 2297 - 2305]

26
[ 106-37-6 ]
[ 18666-68-7 ]
C₄₆H₃₈Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

27
[ 92-86-4 ]
[ 18666-68-7 ]
C₅₂H₄₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

28
[ 28320-32-3 ]
[ 18666-68-7 ]
C₅₅H₄₆Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

29
[ 463944-36-7 ]
[ 18666-68-7 ]
C₈₄H₇₆N₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

30
[ 523-27-3 ]
[ 18666-68-7 ]
9,10-bis[(E)-2-(triphenylsilyl)vinyl]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

31
[ 15155-41-6 ]
[ 18666-68-7 ]
C₄₆H₃₆N₂SSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dicyclohexylmethylamine In toluene at 80℃; for 24h;

Reference： [1]Lo, Mee Yoon; Sellinger, Alan [Synlett, 2006, # 18, p. 3009 - 3012]

32
[ 18666-68-7 ]
[ 18666-87-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: vinyltriphenylsilane With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 3h; Inert atmosphere; Reflux; Stage #2: With sodium peroxoborate tetrahydrate; water In tetrahydrofuran at 45℃; for 3h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: m-chloroperbenzoic acid 2: 86 percent / i-Bu₂AlH / hexane / 1 h

Reference： [1]Location in patent: experimental part Golkowski, Martin; Ziegler, Thomas [Molecules, 2011, vol. 16, # 6, p. 4695 - 4718]
[2]Eisch, John J.; Galle, James E. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 293 - 314]

33
[ 75-94-5 ]
[ 18666-68-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With phenylmagnesium bromide In not given
58%	With C₆H₅MgBr In not given
58%	With C₆H₅MgBr In not given

Reference： [1]Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]
[2]Nagel; Post [Journal of Organic Chemistry, 1952, vol. 17, p. 1379]
[3][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 26, page 80 - 82]

34
[ 18666-68-7 ]
[ 18751-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In not given
	With n-C₄H₉Li In not given

Reference： [1]Gilman et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 3757] Cason; Brooks [Journal of the American Chemical Society, 1952, vol. 74, p. 4582][Journal of Organic Chemistry, 1954, vol. 19, p. 1278]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 26, page 80 - 82]

35
[ 622-30-0 ]
[ 18666-68-7 ]
[ 1093283-34-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium cyanoborohydride In propan-1-ol at 140℃; for 11h; Inert atmosphere; regioselective reaction;

Reference： [1]Moran, Joseph; Gorelsky, Serge I.; Dimitrijevic, Elena; Lebrun, Marie-Eve; Bedard, Anne-Catherine; Seguin, Catherine; Beauchemin, Andre M. [Journal of the American Chemical Society, 2008, vol. 130, # 52, p. 17893 - 17906]

36
[ 1108620-71-8 ]
[ 18666-68-7 ]
[ 1108621-03-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	In benzene at 120℃; for 16h; Autoclave; Inert atmosphere;

Reference： [1]Bourgeois, Joffre; Dion, Isabelle; Cebrowski, Pamela H.; Loiseau, Francis; Bedard, Anne-Catherine; Beauchemin, Andre M. [Journal of the American Chemical Society, 2009, vol. 131, p. 874 - 875]

37
[ 100-53-8 ]
[ 18666-68-7 ]
[ 18870-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]

38
[ 106-45-6 ]
[ 18666-68-7 ]
[ 18870-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]

39
[ 108-98-5 ]
[ 18666-68-7 ]
[ 18758-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid
	Multi-step reaction with 2 steps 1: acetic acid 2: H₂O₂ / acetic acid

Reference： [1]Gilman, H.; Cason, L. F.; Brooks, H. G. [Journal of the American Chemical Society, 1953, vol. 75, p. 3760 - 3762]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 24, page 75 - 77]

40
[ 37059-57-7 ]
[ 18666-68-7 ]
(+)-N-(4-(triphenylsilyl)butan-2-yl)pyridin-2-amine [ No CAS ]
(-)-N-(4-(triphenylsilyl)butan-2-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72 % ee	With bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] In 1,2-dimethoxyethane at 85℃; for 72h; Inert atmosphere; Overall yield = 81 %; enantioselective reaction;	17 N-(4-(Triethylsilyl)butan-2-yl)pyridin-2-amine (3ai) 4.2.17 N-(4-(Triphenylsilyl)butan-2-yl)pyridin-2-amine (3aj) Isolated by thin-layer chromatography (hexane/AcOEt=5/1, Rf=0.4). The title compound was obtained as pale yellow oil (81%). 1H NMR δ 8.05-8.03 (m, 1H), 7.50-7.48 (m, 6H), 7.41-7.32 (m, 10H), 6.53-6.50 (m, 1H), 6.26 (d, J=8.5 Hz, 1H), 4.32 (d, J=8.5 Hz, 1H), 3.76-3.69 (m, 1H), 1.73-1.66 (m, 2H), 1.52-1.36 (m, 2H), 1.18 (d, J=6.3 Hz, 3H); 13C NMR δ 158.3, 148.3, 137.3, 135.6, 134.8, 129.4, 127.9, 112.4, 106.7, 49.5, 30.7, 20.3, 9.0. IR (neat) 3338, 2968, 1603, 1485, 1429, 1290, 1111, 953, 702, 513 cm-1; HRMS(ESI) calcd for C27H29N2Si (M++H): 409.2100; found: 409.2106. [α]D28=9.0 (c 1.01, CHCl3, 72% ee). Ee was determined by HPLC analysis using a chiral column (Daicel Chiralcel OD: 4.6*250 mm, 254 nm UV detector, rt, eluent: 10% isopropanol in hexane, flow rate: 1.0 mL/min, retention time: 5.7 min for minor isomer and 7.1 min for major isomer).

Reference： [1]Pan, Shiguang; Matsuo, Yusuke; Endo, Kohei; Shibata, Takanori [Tetrahedron, 2012, vol. 68, # 44, p. 9009 - 9015]

41
[ 75-05-8 ]
[ 18666-68-7 ]
[ 1426254-40-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-chloro-succinimide; diphenylselenide; water at 25℃; for 18h; Darkness;

Reference： [1]Tay, Daniel Weiliang; Tsoi, Ivan Tan; Er, Jun Cheng; Leung, Gulice Yiu Chung; Yeung, Ying-Yeung [Organic Letters, 2013, vol. 15, # 6, p. 1310 - 1313]

42
[ 73183-34-3 ]
[ 18666-68-7 ]
[ 1449568-90-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With (CH₃Si(C₆H₄P(C₆H₃(CF₃)2)2)2)Pd(SO₃CF₃); triethylaluminum In tetrahydrofuran at 60℃; for 6h; Inert atmosphere; stereoselective reaction;

Reference： [1]Kirai, Naohiro; Iguchi, Shoichiro; Ito, Tatsuyoshi; Takaya, Jun; Iwasawa, Nobuharu [Bulletin of the Chemical Society of Japan, 2013, vol. 86, # 7, p. 784 - 799]

43
[ 1256619-51-8 ]
[ 18666-68-7 ]
[ 1445998-23-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; triethylamine In tetrahydrofuran at 50℃; for 6h;	2.50 g (8.50 mmol) of 7-bromo-9,9-dimethyl-9-h-fluorene-2-ol, 2.43 g (8.50 mmol) of triphenylvinylsilane, 0.19 g (0.21 mmol) of Pd2(dba)3, 1.43 mL (10.2 mmol) of Et3N, and 0.20 g (0.85 mmol) of tri-2-furyl phosphine (TFP) were dissolved in 60 mL of THF and were stirred at a temperature of 50° C. for 6 hours. After the reaction was completed, the reaction product was cooled to room temperature, 40 mL of water was added to the reaction product, and the reaction product was extracted three times with 60 mL of ethylether. The organic layer was collected and then dried using magnesium sulfate, and the solvent was evaporated. The residue was separated and purified using silica gel column chromatography to obtain 3.36 g of Intermediate I-6 (Yield: 80%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2013/168646, 2013, A1 Location in patent: Paragraph 0154; 0155

44
C₂₇H₂₂BrN [ No CAS ]
[ 18666-68-7 ]
[ 1445997-58-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; triethylamine In tetrahydrofuran at 50℃; for 6h;	Synthesis of Compound 11 SYNTHESIS EXAMPLES Synthesis of Compound 11 3.0 g (6.8 mmol) of Intermediate I-1, 1.95 g (6.8 mmol) of triphenylvinylsilane, 0.16 g (0.17 mmol) of Pd2(dba)3, 1.14 mL (8.16 mmol) of Et3N, and 0.16 g (0.68 mmol) of tri-2-furyl phosphine (TFP) were dissolved in 40 mL of THF and were stirred at a temperature of 50° C. for 6 hours. After the reaction was completed, the reaction product was cooled to room temperature, 40 mL of water was added to the reaction product, and the reaction product was extracted three times with 50 mL of ethylether. The organic layer was collected and then dried using magnesium sulfate, and the solvent was evaporated. The residue was separated and purified using silica gel column chromatography to obtain 3.60 g of Compound 11 (Yield: 82%). The obtained compound was confirmed by 1H NMR and MS/FAB. [0144] C47H39NSi: calculated value 645.29, measured value 645.30

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2013/168646, 2013, A1 Location in patent: Paragraph 0141; 0143; 0144

45
[ 1372108-13-8 ]
[ 18666-68-7 ]
[ 1445998-21-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; triethylamine In tetrahydrofuran at 50℃; for 6h;	3.4 g (6.1 mmol) of Intermediate I-4, 1.75 g (6.1 mmol) of triphenylvinylsilane, 0.14 g (0.15 mmol) of Pd2(dba)3, 1.02 mL (7.32 mmol) of Et3N, and 0.14 g (0.61 mmol) of tri-2-furyl phosphine (TFP) were dissolved in 40 mL of THF and then were stirred at a temperature of 50° C. for 6 hours. After the reaction was completed, the reaction product was cooled to room temperature, 40 mL of water was added to the reaction product, and the reaction product was extracted three times with 50 mL of ethylether. The organic layer was collected and then dried using magnesium sulfate, and the solvent was evaporated. The residue was separated and purified using silica gel column chromatography to obtain 3.63 g of Intermediate I-5 (Yield: 78%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2013/168646, 2013, A1 Location in patent: Paragraph 0149; 0151

46
tert-butyl((4-iodopentan-2-yl)oxy)dimethylsilane [ No CAS ]
[ 18666-68-7 ]
C₃₁H₄₄OSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: tert-butyl((4-iodopentan-2-yl)oxy)dimethylsilane With tert.-butyl lithium In diethyl ether; hexane; pentane at -100 - -50℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: vinyltriphenylsilane In diethyl ether; hexane; pentane at -50℃; for 1h; Inert atmosphere; Schlenk technique; diastereoselective reaction;

Reference： [1]Moriya, Kohei; Didier, Dorian; Simon, Meike; Hammann, Jeffrey M.; Berionni, Guillaume; Karaghiosoff, Konstantin; Zipse, Hendrik; Mayr, Herbert; Knochel, Paul [Angewandte Chemie - International Edition, 2015, vol. 54, # 9, p. 2754 - 2757]

47
(E)-N-(4-methoxyphenyl)-1-(1-methyl-1H-indol-3-yl)methanimine [ No CAS ]
[ 18666-68-7 ]
(E)-N-(4-methoxyphenyl)-1-(1-methyl-2-(2-(triphenylsilyl)ethyl)-1H-indol-3-yl)methanimine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(trimethylphosphine)cobalt⁽⁰⁾ In toluene at 170℃; for 1h; Microwave irradiation;

Reference： [1]Fallon, Brendan J.; Derat, Etienne; Amatore, Muriel; Aubert, Corinne; Chemla, Fabrice; Ferreira, Franck; Perez-Luna, Alejandro; Petit, Marc [Organic Letters, 2016, vol. 18, # 9, p. 2292 - 2295]

48
N-(furan-2-ylmethylene)-2-(piperidin-1-yl)ethanamine [ No CAS ]
[ 18666-68-7 ]
3-(2-(triphenylsilyl)ethyl)furan-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With dodecacarbonyl-triangulo-triruthenium In toluene at 150℃; for 16h; Inert atmosphere; Sealed tube;

Reference： [1]Pezzetta, Cristofer; Veiros, Luis F.; Oble, Julie; Poli, Giovanni [Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8385 - 8389]

49
N1-((5-(((tert-butyldimethylsilyl)oxy)methyl)furan-2-yl)methylene)-N2,N2-diethylethane-1,2-diamine [ No CAS ]
[ 18666-68-7 ]
C₃₈H₅₂N₂O₂Si₂ [ No CAS ]
5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(triphenylsilyl)ethyl)furan-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 66 %Spectr.	With dodecacarbonyl-triangulo-triruthenium In toluene at 150℃; for 17h; Inert atmosphere; Sealed tube;

Reference： [1]Pezzetta, Cristofer; Veiros, Luis F.; Oble, Julie; Poli, Giovanni [Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8385 - 8389]

50
[ 694-53-1 ]
[ 18666-68-7 ]
triphenyl(1-(phenylsilyl)ethyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium triethylborohydride In decane; toluene at 100℃; Schlenk technique; regioselective reaction;

Reference： [1]Zaranek; Witomska; Patroniak; Pawluć [Chemical Communications, 2017, vol. 53, # 39, p. 5404 - 5407]

51
[ 775-12-2 ]
[ 18666-68-7 ]
(1-(diphenylsilyl)ethyl)triphenylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium triethylborohydride In decane; toluene at 100℃; Schlenk technique; regioselective reaction;

Reference： [1]Zaranek; Witomska; Patroniak; Pawluć [Chemical Communications, 2017, vol. 53, # 39, p. 5404 - 5407]

52
[ 100-61-8 ]
[ 18666-68-7 ]
N-(2-(triphenylsilyl)propyl)aniline [ No CAS ]
C₂₇H₂₇NSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With C₃₁H₅₃N₅Ti In toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;

Reference： [1]Lühning, Lars H.; Rosien, Michael; Doye, Sven [Synlett, 2017, vol. 28, # 18, p. 2489 - 2494]

53
[ 536-75-4 ]
[ 18666-68-7 ]
4-(4-(triphenylsilyl)butan-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

54
[ 108-89-4 ]
[ 18666-68-7 ]
4-(3-(triphenylsilyl)propyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

55
[ 1122-81-2 ]
[ 18666-68-7 ]
4-(1-(triphenylsilyl)pentan-3-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

56
[ 100-71-0 ]
[ 18666-68-7 ]
2-(4-(triphenylsilyl)butan-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride; In diethyl ether; at 0℃; for 18h;Molecular sieve; Inert atmosphere;	General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Chemistry Letters,2018,vol. 47,p. 690 - 692

57
[ 109-06-8 ]
[ 18666-68-7 ]
2-(3-(triphenylsilyl)propyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

58
[ 583-61-9 ]
[ 18666-68-7 ]
3-methyl-2-(3-(triphenylsilyl)propyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride; In diethyl ether; at 40℃; for 18h;Molecular sieve; Inert atmosphere;	General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Chemistry Letters,2018,vol. 47,p. 690 - 692

59
[ 108-47-4 ]
[ 18666-68-7 ]
C₂₇H₂₇NSi [ No CAS ]
2-methyl-4-(3-(triphenylsilyl)propyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere; Overall yield = 88 %; regioselective reaction;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

60
[ 5709-61-5 ]
[ 18666-68-7 ]
1-methyl-2-(4-(triphenylsilyl)butan-2-yl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 0℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

61
[ 1721-93-3 ]
[ 18666-68-7 ]
1-(3-(triphenylsilyl)propyl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 60℃; for 48h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

62
[ 1613-34-9 ]
[ 18666-68-7 ]
2-(4-(triphenylsilyl)butan-2-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium chloride In diethyl ether at 60℃; for 18h; Molecular sieve; Inert atmosphere;	Experimental procedure of catalytic addition reaction of 4-ethylpyridine (2a) withTriphenylvinylsilane (1a) General procedure: A solution of LiTMP (0.03 mmol), LiCl (0.03 mmol) and MS4A (30 mg) in Et2O (0.1 mL) in a flame dried 10 mL flask with 3-way stopcock sealed by grease was stirred for 30 minutes at 0 °C under Ar atmosphere. 4-Ethylpyridine (2a) (0.36 mmol) was added, and the mixture was stirred at 0 °C. Vinylsilane 1a (0.3 mmol) in Et2O (0.4 mL) was then added, and the mixture was stirred for 18 h at 0 °C. The reaction was quenched with brine (1 mL), and the aqueous layer was extracted with dichloromethane (10 mL x 3) after separation of the organic layer. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure after filtration. The residue was purified by PTLC with hexane-DCM-Et2O (3:3:2) as an eluent to give the desired product 3aa.

Reference： [1]Yamashita, Yasuhiro; Minami, Kodai; Kobayashi, Shu [Chemistry Letters, 2018, vol. 47, # 5, p. 690 - 692]

63
[ 4553-05-3 ]
[ 18666-68-7 ]
2-methyl-1-(pyrrolidin-1-yl)-4-(triphenylsilyl)butan-1-one [ No CAS ]