Issue 93, 2022

Catalytic O2 activation toward oxidative N–S bond formation by a thiolato Fe(iii) complex

Abstract

Compounds with the benzisothiazol-3-one (BIT) skeleton perform excellently in the pharmaceutical field, although current synthetic methods remain limited in terms of synthetic efficiency. Herein, we report the catalytic intramolecular N–S bond formation for BITs from easily prepared disulfide precursors by an Fe(III) dithiolate through O2 activation at 298 K. Interestingly, the catalytic performance is enhanced by substituting O2 with a milder O-donor oxidant, ONMe3. Catalytic oxygenation of PPh3 to OPPh3 can also proceed under similar conditions. In addition, the first anionic monosulfenato Fe(III) species, Fe(III)–S([double bond, length as m-dash]O)R, is isolated with structural characterization from the reaction of Fe(III) thiolate and ONMe3.

Graphical abstract: Catalytic O2 activation toward oxidative N–S bond formation by a thiolato Fe(iii) complex

Supplementary files

Article information

Article type
Communication
Submitted
01 Oct 2022
Accepted
25 Oct 2022
First published
26 Oct 2022

Chem. Commun., 2022,58, 12943-12946

Catalytic O2 activation toward oxidative N–S bond formation by a thiolato Fe(III) complex

C. Hsieh, C. Li, M. Chiang and Y. Horng, Chem. Commun., 2022, 58, 12943 DOI: 10.1039/D2CC05375F

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