Issue 2, 2018

Highly mono-selective ortho-methylthiolation of benzamides via cobalt-catalyzed sp2 C–H activation

Abstract

A highly mono-selective ortho-methylthiolation of benzamides was achieved via Co-catalyzed coupling of benzamides with DMSO. The reaction employs an 8-aminoquinoline group as the bidentate directing group and DMSO as the methylthiolation source. Instead of a mixture of mono- and di-alkylthio-substituted products obtained by previously reported procedures, our reaction gave the mono-methylthioethers only. Another notable feature of this newly developed protocol is that acrylamides can also be efficiently mono-methylthiolated.

Graphical abstract: Highly mono-selective ortho-methylthiolation of benzamides via cobalt-catalyzed sp2 C–H activation

Supplementary files

Article information

Article type
Research Article
Submitted
14 Aug 2017
Accepted
30 Sep 2017
First published
09 Oct 2017

Org. Chem. Front., 2018,5, 216-221

Highly mono-selective ortho-methylthiolation of benzamides via cobalt-catalyzed sp2 C–H activation

L. Hu, X. Chen, L. Yu, Y. Yu, Z. Tan, G. Zhu and Q. Gui, Org. Chem. Front., 2018, 5, 216 DOI: 10.1039/C7QO00717E

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