Copper-Catalyzed Regiodivergent Silacarboxylation of Allenes with Carbon Dioxide and a Silylborane

被引：119

作者：

Tani, Yosuke ^{[1
]}

Fujihara, Tetsuaki ^{[1
]}

Terao, Jun ^{[1
]}

Tsuji, Yasushi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 51期

关键词：

SILYL-CUPRATION; HYDROGEN-PEROXIDE; ORGANIC-SYNTHESIS; CARBOXYLATION; SILYLCUPRATION; ALLYLSILANES; ALKYNES; NICKEL; VINYLSILANES; DERIVATIVES;

D O I：

10.1021/ja512040c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A regiodivergent silacarboxylation of allenes under a CO2 atmosphere with PhMe2Si-B(pin) as a silicon source in the presence of a copper catalyst at 70 degrees C has been developed. The regioselectivity of the reaction is successfully reversed by the proper choice of ligand; carboxylated vinylsilanes are obtained with rac-Me-DuPhos as the ligand, whereas the use of PCy3 affords carboxylated allylsilanes. Thus, two different carboxylated silanes can be selectively and regiodivergently synthesized from a single allene substrate.

引用

页码：17706 / 17709

页数：4

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