The Fascinating Chemistry of α-Haloamides
Anna Fantinati1, Vinicio Zanirato1, Paolo Marchetti1
1Department of Chemical and Pharmaceutical Sciences University of Ferrara, Via Fossato di Mortara 17 44121 Ferrara Italy E-mail: V. Zanirato.
Abstract:
The aim of this review is to highlight the rich chemistry of α-haloamides originally mainly used to discover new C-N, C-O and C-S bond forming reactions, and later widely employed in C-C cross-coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical-mediated transformations of α-haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α-halohydroxamate-based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.
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