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Photoredox-mediated remote C(sp³)-H heteroarylation of free alcohols.

ABSTRACT: We report an efficient and economical method for remote ? C(sp³)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at ? methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.

SUBMITTER: Li GX

PROVIDER: S-EPMC6345347 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Photoredox-mediated remote C(sp3)-H heteroarylation of free alcohols.

Li Guo-Xing GX Hu Xiafei X He Gang G Chen Gong G

Chemical science 20181030 3

We report an efficient and economical method for remote δ C(sp3)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has b ...[more]

PMID: 30774869

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