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RESEARCH ARTICLE
Contents Vol 77(1)

Cobalt(II) catalytic oxidation of arylmethyl sulfonyl imines to arylcarbonyl analogues

Zetao Ma A , Peipei Ma A , Hongli Wu A and Haifeng Gan https://orcid.org/0000-0001-9433-0542 A *
+ Author Affiliations
- Author Affiliations

A College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 211816, PR China.

* Correspondence to: ganhaifeng@njtech.edu.cn

Handling Editor: Paul Bernhardt

Australian Journal of Chemistry 77, CH23190 https://doi.org/10.1071/CH23190
Submitted: 13 October 2023  Accepted: 8 December 2023  Published online: 8 January 2024

© 2024 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

A novel Co(OAc)2/N-hydroxyphthalimide (NHPI)-catalyzed oxidation of 3-arylmethyl sulfonyl imines to prepare 3-arylcarbonyl analogues has been realized. 3-Arylcarbonyl sulfonyl imines were comprehensively synthesized from benzyl substrates for the first time. The reactions proceeded in moderate to excellent yields. Mechanistic investigation suggests that 3-(hydroperoxy(phenyl)methyl)benzo[d]isothiazole 1,1-dioxide A is the key intermediate for the formation of products 2.

Keywords: Co(OAc)2, dioxygen, mechanism, NHPI, oxidation, pharmaceutical, radical, sulfonyl imines.

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