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

Chong Mei; Yixin Hu; Wenjun Lu

doi:10.1055/s-0036-1591575

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(15): 2999-3005
DOI: 10.1055/s-0036-1591575

special topic

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

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Abstract

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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.

Key words

imides - amides - oxidation - catalysis - photochemistry

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