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Photo‐Mediated Intermolecular Coupling of Alkenes with Ketones via Acyloxy Nitroso Compounds
Author(s) -
Zheng Danqing,
Plöger Stefanie,
Daniliuc Constantin G.,
Studer Armido
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016955
Subject(s) - chemistry , intermolecular force , nitroso , ketone , nitroso compounds , oxidative coupling of methane , photochemistry , coupling (piping) , cascade , medicinal chemistry , organic chemistry , catalysis , molecule , mechanical engineering , chromatography , engineering
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.