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Issue 7, 2016
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Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis

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Abstract

Although visible light photoredox catalysis has emerged as a powerful tool for the construction of C–C bonds, common catalysts and/or their photoexcited states suffer from low redox potentials, limiting their applicability to alkyl radical generation from substrates with activated carbon–halogen bonds. Radicals derived from these activated compounds, being highly electrophilic or stabilized, do not undergo efficient addition to heteroarenes. Herein we describe the photocatalytic generation of nucleophilic alkyl radicals from unactivated bromoalkanes as part of a universal and efficient cross-coupling strategy for the direct alkylation of heteroarenes using a dimeric gold(I) photoredox catalyst, [Au2(bis(diphenylphosphino)methane)2]Cl2. The method proves to be efficient for alkylation of arenes under mild conditions in the absence of directing groups.

Graphical abstract: Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis

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Publication details

The article was received on 21 Feb 2016, accepted on 15 Apr 2016 and first published on 18 Apr 2016


Article type: Edge Article
DOI: 10.1039/C6SC00807K
Citation: Chem. Sci., 2016,7, 4754-4758
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    Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis

    T. McCallum and L. Barriault, Chem. Sci., 2016, 7, 4754
    DOI: 10.1039/C6SC00807K

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