Katarzyna N Lee1, Ming-Yu Ngai. 1. Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, USA. ming-yu.ngai@stonybrook.edu.
Abstract
Single-electron reduction of C[double bond, length as m-dash]O and C[double bond, length as m-dash]N bonds of aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecules and undergo a diverse range of synthetically useful transformations, which are not available to even-electron species. This Review summarizes the reactions of ketyl and α-aminyl radicals generated from carbonyl derivatives under transition-metal photoredox-catalysed conditions. We primarily focus on recent developments in the field, as well as give a brief overview of catalytic enantioselective transformations that provide a means to achieve precise stereocontrol over the reactivity of ion radicals.
Single-electron reduction of C[double bond, length as m-dash]O and C[double bond, length as m-dash]N bonds of n class="Chemical">aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecules and undergo a diverse range of synthetically useful transformations, which are not available to even-electron species. This Review summarizes the reactions of ketyl and α-aminyl radicals generated from carbonyl derivatives under transition-metal photoredox-catalysed conditions. We primarily focus on recent developments in the field, as well as give a brief overview of catalytic enantioselective transformations that provide a means to achieve precise stereocontrol over the reactivity of ion radicals.
Authors: Lydia J Rono; Hatice G Yayla; David Y Wang; Michael F Armstrong; Robert R Knowles Journal: J Am Chem Soc Date: 2013-11-13 Impact factor: 15.419
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