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

Guo Xing Li, Cristian A. Morales-Rivera, Fang Gao, Yaxin Wang, Gang He, Peng Liu, Gong Chen

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7180-7185
Number of pages6
JournalChemical Science
Volume8
Issue number10
DOIs
StatePublished - 2017

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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