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A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

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Abstract

We report a unified photoredox-catalysis strategy for both hydroxylation and amidation of tertiary and benzylic C–H bonds. Use of hydroxyl perfluorobenziodoxole (PFBl–OH) oxidant is critical for efficient tertiary C–H functionalization, likely due to the enhanced electrophilicity of the benziodoxole radical. Benzylic methylene C–H bonds can be hydroxylated or amidated using unmodified hydroxyl benziodoxole oxidant Bl–OH under similar conditions. An ionic mechanism involving nucleophilic trapping of a carbocation intermediate by H2O or CH3CN cosolvent is presented.

Graphical abstract: A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

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Publication details

The article was received on 21 Jun 2017, accepted on 02 Sep 2017 and first published on 04 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02773G
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

    G. Li, C. A. Morales-Rivera, F. Gao, Y. Wang, G. He, P. Liu and G. Chen, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02773G

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