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Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides.

ABSTRACT: The emergence of photoredox catalysis has enabled the discovery of mild and efficient conditions for the generation of a variety of radical reaction platforms. Herein is disclosed the development of a conjugate addition reaction of non-activated alkyl bromides to Michael acceptors under visible-light photoredox catalysis. Optimization of the reaction was achieved using high-throughput experimentation (HTE) tools to enable the identification of mild, general and practical reaction conditions. A diverse set of alkyl bromides was successfully added to cyclic or acyclic ?,?-unsaturated esters and amides. The features of this transformation allowed also access to a key intermediate of Vorinostat®, an HDAC inhibitor used to fight cancer and HIV.

SUBMITTER: ElMarrouni A

PROVIDER: S-EPMC6115631 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides.

ElMarrouni Abdellatif A Ritts Casey B CB Balsells Jaume J

Chemical science 20180711 32

The emergence of photoredox catalysis has enabled the discovery of mild and efficient conditions for the generation of a variety of radical reaction platforms. Herein is disclosed the development of a conjugate addition reaction of non-activated alkyl bromides to Michael acceptors under visible-light photoredox catalysis. Optimization of the reaction was achieved using high-throughput experimentation (HTE) tools to enable the identification of mild, general and practical reaction conditions. A d ...[more]

PMID: 30310596

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