Synthesis 2018; 50(15): 2999-3005
DOI: 10.1055/s-0036-1591575
special topic
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Driven Oxidation of N-Alkylamides to Imides Using Oxone/H2O and Catalytic KBr

Chong Mei
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
,
Yixin Hu
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
,
Wenjun Lu  *
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
› Author Affiliations
We thank the National Natural Science Foundation of China (Grant No. 21372153) for financial support.
Further Information

Publication History

Received: 26 February 2018

Accepted after revision: 03 April 2018

Publication Date:
16 May 2018 (online)


Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

Imides are prepared conveniently by visible-light-driven oxidations of various N-alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H2O/CH2Cl2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.

Supporting Information

 
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