Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis

被引：66

作者：

Perkowski, Andrew J. ^{[1
]}

Cruz, Cole L. ^{[1
]}

Nicewicz, David A. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, CB 3290, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 50期

关键词：

ANTI-MARKOVNIKOV ADDITION; O-ARYL; SCHONBERG REARRANGEMENT; MICROWAVE SYNTHESIS; C-S; THIONCARBONATES; THIOPHENOLS; ANTAGONIST; CONVERSION; MECHANISM;

D O I：

10.1021/jacs.5b11800

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Newman-Kwart rearrangement is perhaps the quintessential method for the synthesis of thiophenols from the corresponding phenol. However, the high thermal conditions required for the rearrangement of the requisite O-aryl carbamothioates often leads to decomposition. Herein, we present a general strategy for catalysis of O-aryl carbamothioates to S-aryl carbamothioates using catalytic quantities of a commercially available organic single-electron photooxidant. Importantly, this reaction is facilitated at ambient temperatures.

引用

页码：15684 / 15687

页数：4

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