Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 5, Pages 1565-1569Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410432
Keywords
alkylation; C-H functionalization; ethers; heterocycles; photoredox catalysis
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Funding
- NIH General Medical Sciences (Grant NIHGMS) [R01 GM103558-03]
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The direct alpha-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated C-H functionalization pathway. Transiently generated alpha-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.
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