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

作者:Perkowski Andrew J; Cruz Cole L; Nicewicz David A*
来源:Journal of the American Chemical Society, 2015, 137(50): 15684-15687.
DOI:10.1021/jacs.5b11800

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.

  • 出版日期2015-12-23