Issue 24, 2021

Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C–N bond formation

Abstract

A new methodology to synthesize sulfonyl-N-phenylaniline derivatives via the trapping of bromo-sulfone derivatives generated from N-tosylhydrazones (NTHs) with amines is described. The reaction proved successful for a wide range of NTHs and amines and tolerated various functional groups on either coupling partner (35 examples). The mechanism was studied, and we showed that the sulfone formation does not follow a radical pathway.

Graphical abstract: Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C–N bond formation

Supplementary files

Article information

Article type
Paper
Submitted
07 Apr 2021
Accepted
26 May 2021
First published
26 May 2021

Org. Biomol. Chem., 2021,19, 5358-5367

Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C–N bond formation

K. Zhang, O. Provot, C. Tran, M. Alami and A. Hamze, Org. Biomol. Chem., 2021, 19, 5358 DOI: 10.1039/D1OB00676B

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