Application of fluoride-catalyzed silane reductions of tin halides to the in situ preparation of vinylstannanes

被引：31

作者：

Maleczka, RE ^{[1
]}

Terrell, LR ^{[1
]}

Clark, DH ^{[1
]}

Whitehead, SL ^{[1
]}

Gallagher, WP ^{[1
]}

Terstiege, I ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 16期

关键词：

D O I：

10.1021/jo990491+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have found that either Bu3SnCl/PMHS/KF(aq), or the combination of tributyltin fluoride, PMHS, and catalytic quantities of tetrabutylammonium fluoride can serve as in situ sources of tributyltin hydride for both free radical and palladium-catalyzed hydrostannylation reactions. These methods are tolerant of a variety of functional groups, including silyl ethers, Furthermore, Me3SnCl is also reduced under these conditions, providing a relatively convenient and safe manner by which Me3SnH can be formed and reacted. We have also observed that the Bu3SnCl/siloxane/fluoride combination offers improvements over the existing protocols for transforming 1-bromoalkynes into trans-1-(tributylstannyl)-1-alkenes. Specifically, the KF/PMHS methodology allows the 1-bromoalkyne to be formed and reacted in a single pot and with substoichiometric amounts of tin. Finally, alternative reductants such as Red-Sil are also amenable to the method.

引用

页码：5958 / 5965

页数：8

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