The formation of Csp3-Csp3 bonds remains one of the most challenging synthetic transformations in organic synthesis. The development of general and modular synthetic methods requiring minimal activating groups for reactivity has the potential to dramatically expand the structure-activity relationship (SAR) toolbox of the medicinal chemist and impact the discovery of new small molecule therapeutics. The emergence of photoredox catalysis has enabled the discovery of mild and efficient conditions for the generation of organic radicals. Our group has recently developed a new methodology relying on a conjugate addition reaction of alkyl bromides to amides and esters under visible-light catalysis. While the generation of these radicals under photoredox conditions has been reported by the MacMillan group, conjugate addition reactions of these radicals has not been reported to date. Extensive optimization using high-throughput experimentation (HTE) tools enabled the identification of general and practical reaction conditions. The addition of unactivated primary, secondary and tertiary alkyl bromides to several cyclic or acyclic α,β–unsaturated esters and amides has been accomplished. The optimization and scope of this transformation will be presented

Radical conjugate addition of alkyl bromides to α,β-unsaturated amides and esters by visible-light photoredox catalysis

254th National Meeting (2017)

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