Issue 15, 2019

Transition metal-free α-Csp3–H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides

Abstract

A metal-free approach to N-aryl thioamides from Bunte salts and anilines in DMSO has been developed. This method tolerated a wide range of functional groups on the aromatic ring, providing an ideal way to N-aryl thioamides in good to excellent yields from cheap and easily available starting materials. A plausible mechanism was also proposed based on the X-ray single crystal diffraction, NMR and MS analyses of DMSO-concerning intermediates.

Graphical abstract: Transition metal-free α-Csp3–H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides

Supplementary files

Article information

Article type
Paper
Submitted
11 Feb 2019
Accepted
18 Mar 2019
First published
19 Mar 2019

Org. Biomol. Chem., 2019,17, 3790-3796

Transition metal-free α-Csp3–H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides

M. Qiao, J. Zhang, L. Chen, F. Zhou, Y. Zhang, L. Zhou and Y. Wu, Org. Biomol. Chem., 2019, 17, 3790 DOI: 10.1039/C9OB00336C

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