Transition Metal-Free Amidoalkylation of Benzothiazoles and Amidoalkylarylation of Activated Alkenes with N,N-Dialkylamides

J Org Chem. 2016 Apr 1;81(7):3017-22. doi: 10.1021/acs.joc.6b00096. Epub 2016 Mar 22.

Abstract

A general and practical amidoalkylation reaction, using N,N-dialkylamides in the presence of potassium persulfate as the sole reagent, has been developed. 2-Amidoalkylated benzothiazole- and 3-amidoalkyl-substituted indolinone derivatives were obtained by using benzothiazoles and N-aryl-N-methyl-methacrylamides as substrates, respectively. The transformation proceeded smoothly through amidoalkyl radical intermediates that were trapped by benzothiazoles or activated alkenes.

Publication types

  • Research Support, Non-U.S. Gov't