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Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis.

ABSTRACT: A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

SUBMITTER: Rivero AR

PROVIDER: S-EPMC7653678 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis.

Rivero Alexandra R AR Fodran Peter P Ondrejková Alica A Wallentin Carl-Johan CJ

Organic letters 20201011 21

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, ...[more]

PMID: 33040526

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