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. 2015 Jan 26;54(5):1565-9.
doi: 10.1002/anie.201410432. Epub 2014 Dec 2.

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

Jian Jin  1 , David W C MacMillan
Affiliations

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

Jian Jin et al. Angew Chem Int Ed Engl. .

Abstract

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 using feedstock substrates and a commercial photocatalyst.

Keywords: CH functionalization; alkylation; ethers; heterocycles; photoredox catalysis.

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Figures

Figure 1
Figure 1
Photoredox mediated C–H functionalization.
Scheme 1
Scheme 1
Proposed mechanism for α–arylation of ethers.
See this image and copyright information in PMC

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