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

Alexandra R. Rivero | Zendy; Peter Fodran | Zendy; Alica Ondrejková | Zendy; CarlJohan Wallentin | Zendy

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

Author(s) -

Alexandra R. Rivero,

Peter Fodran,

Alica Ondrejková,

CarlJohan Wallentin

Publication year - 2020

Publication title -

organic letters

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03058

Subject(s) - photoredox catalysis , chemistry , hypervalent molecule , radical , alkoxy group , catalysis , reagent , alkyl , photochemistry , aryl , alcohol , visible spectrum , combinatorial chemistry , hydrogen atom , organic chemistry , photocatalysis , physics , optoelectronics

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(sp 3 )-H and C(sp 2 )-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.

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