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

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Abstract

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 been successfully applied to modification of complex drug molecules.

Graphical abstract: Photoredox-mediated remote C(sp3)–H heteroarylation of free alcohols

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Publication details

The article was received on 17 Sep 2018, accepted on 27 Oct 2018 and first published on 30 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC04134B
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Photoredox-mediated remote C(sp3)–H heteroarylation of free alcohols

    G. Li, X. Hu, G. He and G. Chen, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04134B

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