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Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis.

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.

SUBMITTER: McCallum T

PROVIDER: S-EPMC6016576 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis.

McCallum T T Barriault L L

Chemical science 20160418 7

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 nu ...[more]

PMID: 30155127

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