Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 15, Pages 8547-8551Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016955
Keywords
Barton reaction; carbon radicals; nitroso compounds; persistent radical effect; radical cascade
Categories
Funding
- University of Munster
- Fonds der Chemischen Industrie
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An atom-economic intermolecular radical addition reaction of acyloxy nitroso compounds to electron-deficient alkenes mediated by visible light has been successfully reported, providing a series of valuable functionalized oximes in moderate to good yields. Mechanistic studies suggest that these cascades proceed via addition/coupling processes controlled by the persistent radical effect (PRE) with NO acting as the persistent species.
An atom-economic intermolecular radical addition reaction of acyloxy nitroso compounds to electron-deficient alkenes mediated by visible light is reported. The starting nitroso derivatives are readily prepared by oxidation of the corresponding oximes prepared from ketones and the overall transformation represents an oxidative coupling of a ketone with a Michael acceptor. The cascade proceeds smoothly under mild conditions, providing a series of valuable functionalized oximes in moderate to good yields. Mechanistic studies suggest that these cascades proceed via addition/coupling processes that are controlled by the persistent radical effect (PRE) with NO acting as the persistent species.
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