Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 18, Pages 5166-5170Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800375
Keywords
amination; bromine; catalysis; C-H functionalization; Hofmann-Loffler reaction
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Funding
- Spanish Ministry for Economy and Competitiveness
- FEDER [CTQ2017-88496R]
- FEDER (Severo Ochoa Excellence Accreditation) [SEV-2013-0319]
- COST Action C-H Activation in Organic Synthesis (CHAOS) [CA15106]
- Alexander von Humboldt Foundation
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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(sp(3))-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-Loffler 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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