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Direct ?-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

ABSTRACT: The direct ?-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated C?H functionalization pathway. Transiently generated ?-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst.

SUBMITTER: Jin J

PROVIDER: S-EPMC4311771 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

Jin Jian J Jin Jian J MacMillan David W C DW

Angewandte Chemie (International ed. in English) 20141202 5

The direct α-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated CH functionalization pathway. Transiently generated α-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility usin ...[more]

PMID: 25470570

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