Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis

被引：176

作者：

Terrett, Jack A. ^{[1
]}

Clift, Michael D. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 19期

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; CATALYSIS; ARYLATION; RADICALS; ACTIVATION; OXIDATION; KETONES; TRIFLUOROMETHYLATION; FUNCTIONALIZATION; STRATEGY;

D O I：

10.1021/ja502639e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct beta-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce beta-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.

引用

页码：6858 / 6861

页数：4

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