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Issue 32, 2018
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Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides

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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 α,β-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.

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

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Publication details

The article was received on 22 May 2018, accepted on 06 Jul 2018 and first published on 11 Jul 2018


Article type: Edge Article
DOI: 10.1039/C8SC02253D
Citation: Chem. Sci., 2018,9, 6639-6646
  • Open access: Creative Commons BY-NC license
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    Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides

    A. ElMarrouni, C. B. Ritts and J. Balsells, Chem. Sci., 2018, 9, 6639
    DOI: 10.1039/C8SC02253D

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