Dual Role of Silanol Groups in Cyclopropanation and Hiyama-Denmark Cross-Coupling Reactions

被引：21

作者：

Beaulieu, Louis-Philippe B. ^{[1
]}

Delvos, Lukas B. ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Stn Downtown Montreal, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

CONTAINING NATURAL-PRODUCTS; ARYL HALIDES; SUZUKI COUPLINGS; SILICON; SUBSTITUENTS; OLEFINS; ESTERS; ALKYLTRIFLUOROSILANES; ALKENYLSILANOLS; VINYLSILANES;

D O I：

10.1021/ol1002863

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Di-tert-butoxy(alkenyl)silanols serve as substrates in the Simmons-Smith cyclopropanation reaction furnishing the corresponding di-tert-butoxy(cyclopropyl)silanols, which may be included in a Hiyama-Denmark cross-coupling reaction. The silanol group bears two distinct roles as it provides a directing group during the cyclopropanation and mediates the transmetalation event in the cross-coupling. The nature of the ligands on the silicon atom had a profound effect on reactivity in the cross-coupling, whereby substituting the alkoxide groups for fluorides allowed for efficient cross-coupling.

引用

页码：1348 / 1351

页数：4

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