Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

被引：96

作者：

Kosal, Andrew D. ^{[1
]}

Wilson, Erin E. ^{[1
]}

Ashfeld, Brandon L. ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 48期

基金：

美国国家科学基金会;

关键词：

amides; azides; carboxylic acids; homogeneous catalysis; Staudinger ligation; WITTIG REACTION; ACYL SUBSTITUTION; APPEL REACTION; REDUCTION; PEPTIDE; REAGENT; PHENYLSILANE; DERIVATIVES; ACTIVATION; PROTEINS;

D O I：

10.1002/anie.201206533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in C-N bond formation. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12036 / 12040

页数：5

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