Silylboranes bearing dialkylamino groups on silicon as silylene equivalents: Palladium-catalyzed regioselective synthesis of 2, 4-disubstituted siloles

T Ohmura, K Masuda, M Suginome

Index: Ohmura, Toshimichi; Masuda, Kohei; Suginome, Michinori Journal of the American Chemical Society, 2008 , vol. 130, # 5 p. 1526 - 1527

Full Text: HTML

Citation Number: 49

Abstract

Silylpinacolboranes bearing dialkylamino groups on the silicon atom served as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon ...

Related Articles:

A Controlled, Iterative Synthesis and the Electronic Properties of Oligo [(p-phenyleneethynylene)-a lt-(2, 5-siloleneethynylene)] s

[Boydston, Andrew J.; Yin, Youshi; Pagenkopf, Brian L. Journal of the American Chemical Society, 2004 , vol. 126, # 33 p. 10350 - 10354]

(Trialkylstannyl) dimethylsilane as a new precursor of dimethylsilylene: a novel synthesis of 3, 4-disubstituted 1-silacyclopenta-2, 4-dienes

[Ikenaga, Kazutoshi; Hiramatsu, Kouji; Nasaka, Norimitsu; Matsumoto, Satoshi Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5045 - 5047]

Diels-Alder reactions of 1, 1-dimethyl-2, 3, 4, 5-tetraphenyl-1-silacyclopentadiene, 1, 1-dimethyl-2, 5-diphenyl-1-silacyclopentadiene and 1, 1-dimethyl-3, 4-diphenyl-1 …

[Henry, George K.; Shinimoto, Ronald; Zhou, Qingshan; Weber, William P. Journal of Organometallic Chemistry, 1988 , vol. 350, p. 3 - 8]

Diels-Alder reactions of 1, 1-dimethyl-2, 3, 4, 5-tetraphenyl-1-silacyclopentadiene, 1, 1-dimethyl-2, 5-diphenyl-1-silacyclopentadiene and 1, 1-dimethyl-3, 4-diphenyl-1 …

[Henry, George K.; Shinimoto, Ronald; Zhou, Qingshan; Weber, William P. Journal of Organometallic Chemistry, 1988 , vol. 350, p. 3 - 8]

More Articles...