Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

被引：170

作者：

Le Vaillant, Franck ^{[1
]}

Courant, Thibaut ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, EPFL SB ISIC LCSO, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 38期

基金：

欧洲研究理事会;

关键词：

alkynes; amino acids; carboxylic acids; hypervalent iodine; photocatalysis; HYPERVALENT IODINE REAGENTS; ALPHA-AMINO-ACIDS; C-H ALKYNYLATION; MERGING PHOTOREDOX; CHEMOSELECTIVE ALKYNYLATION; SONOGASHIRA REACTION; ONE-POT; LIGHT; GOLD; ALKENES;

D O I：

10.1002/anie.201505111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with ethynylbenziodoxolone (EBX) reagents allowed the decarboxylative alkynylation of carboxylic acids in good yields under mild conditions. The method could be applied to silyl-, aryl-, and alkyl- substituted alkynes. It was particularly successful in the case of alpha-amino and alpha-oxo acids derived from biomass.

引用

页码：11200 / 11204

页数：5

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