Open AccessVisible Light-Induced Pd-Catalyzed Alkyl-Heck Reaction of Oximes
Author(s) -
Nikita Kvasovs,
Valeriia Iziumchenko,
Vitalii A. Palchykov,
Vladimir Gevorgyan
Publication year - 2021
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.1c00267
Subject(s) - alkyl , chemistry , moiety , catalysis , palladium , alkylation , nucleophile , imine , photochemistry , photoredox catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry , photocatalysis
A visible light-induced palladium-catalyzed oxidative C-H alkylation of oximes has been developed. This mild protocol allows for an efficient atom economical C-C bond construction of alkyl-substituted oximes. A broad range of primary, secondary, and tertiary alkyl bromides and iodides, as well as a range of different formaldoximes, can efficiently undergo this transformation. The method features visible light-induced generation of nucleophilic hybrid alkyl Pd radical intermediates, which upon radical addition at the imine moiety and a subsequent β -hydrogen elimination deliver substituted imines.