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Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient Olefins

Author:
Slutskyy, Yuriy, Overman, Larry E.
Source:
Organic letters 2016 v.18 no.11 pp. 2564-2567
ISSN:
1523-7052
Subject:
Lewis bases, alkenes, catalytic activity, chemical structure, free radicals, oxalates, redox reactions, regioselectivity
Abstract:
Visible-light photoredox-catalyzed fragmentation of methyl N-phthalimidoyl oxalate allows the direct construction of a 1,4-dicarbonyl structural motif by a conjugate addition of the methoxycarbonyl radical to reactive Michael acceptors. The regioselectivity of the addition of this alkoxyacyl radical species to electron-deficient olefins is heavily influenced by the electronic nature of the acceptor, behavior similar to that exhibited by nucleophilic alkyl radicals.
Agid:
5790663