Iridium-catalyzed Reductive Nucleophilic Addition to Tertiary Amides

被引：37

作者：

Takahashi, Yoshito ^{[1
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

来源：

CHEMISTRY LETTERS | 2019年 / 48卷 / 09期

关键词：

Amides; Iridium catalyst; Nucleophilic addition; CHEMOSELECTIVE REDUCTION; ORGANOMETALLIC REAGENTS; SEQUENTIAL REACTIONS; SECONDARY AMIDES; ORGANOLITHIUM; ALDEHYDES; GRIGNARD; HYDROZIRCONATION; (+/-)-GEPHYROTOXIN; LACTAMS/AMIDES;

D O I：

10.1246/cl.190467

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article describes the development of an iridium-catalyzed reductive nucleophilic addition to tertiary amides. A conspicuous feature of this reaction is its high amide-selectivity via two processes: i) chemoselective hydrosilylation of amide carbonyls with Vaska's complex [IrCl(CO)(PPh3)(2)] and (Me2HSi)(2)O, and ii) subsequent addition of a variety of mild nucleophiles to the resulting electrophilic iminium ions by the assistance of an acid. The reaction takes place in the presence of a variety of functional groups such as ester and nitro groups.

引用

页码：1138 / 1141

页数：4

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