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Direct α‐Arylation of Ethers through the Combination of Photoredox‐Mediated CH Functionalization and the Minisci Reaction
Author(s) -
Jin Jian,
MacMillan David W. C.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410432
Subject(s) - surface modification , chemistry , radical , photoredox catalysis , pharmacophore , combinatorial chemistry , hydrogen atom , photochemistry , photocatalysis , organic chemistry , stereochemistry , catalysis , alkyl
The direct α‐arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox‐mediated CH 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 using feedstock substrates and a commercial photocatalyst.