Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C-H Bond Functionalization

Angewandte Chemie
Peter BeckerKilian Muniz

Abstract

The potential of homogeneous oxidation catalysis employing bromine has remained largely unexplored. We herein show that the combination of a tetraalkylammonium bromide and meta-chloroperbenzoic acid offers a unique catalyst system for the convenient and selective oxidation of saturated C(sp3 )-H bonds upon photochemical initiation with day light. This approach enables remote, intramolecular, position-selective C-H amination as demonstrated for 20 different examples. For the first time, an N-halogenated intermediate was isolated as the active catalyst state in a catalytic Hofmann-Löffler reaction. In addition, an expeditious one-pot synthesis of N-sulfonyl oxaziridines from N-sulfonamides was developed and exemplified for 15 transformations. These pioneering examples provide a change in paradigm for molecular catalysis with bromine.

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Citations

Sep 7, 2018·Chemistry : a European Journal·Estefanía Del CastilloKilian Muñiz
Jul 18, 2019·Angewandte Chemie·Ming-Ming Wang, Jérôme Waser
Feb 6, 2020·Chemistry, an Asian Journal·Gautam KumarIndranil Chatterjee
Mar 27, 2021·Chemistry : a European Journal·Liejin ZhouZuxiao Zhang
Nov 8, 2019·Journal of the American Chemical Society·Atanu ModakSilas P Cook
Feb 20, 2019·The Journal of Organic Chemistry·Suraj K Ayer, J L Roizen
Dec 12, 2018·The Journal of Organic Chemistry·Yan-Na MaXuenian Chen
Mar 25, 2020·Organic Letters·Qing-Qiang MinFeng Liu
Aug 14, 2019·The Journal of Organic Chemistry·Yan-Na MaXuenian Chen
Jul 31, 2021·Angewandte Chemie·Yanis LazibPhilippe Dauban
Apr 11, 2020·The Journal of Organic Chemistry·Nallappan SundaraveluGovindasamy Sekar
Jan 24, 2019·Organic Letters·Estefanía Del Castillo, Kilian Muñiz
Oct 8, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yan GaoYan-Na Ma

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