Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

29 May 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry.

Keywords

photoredox reactions
copper
alcohols
ethers
radical
Benzylic functionalization

Supplementary materials

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Description
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Title
LeeDeGlopper SI
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