A unified photoredox-catalysis strategy for C(sp3)-H hydroxylation and amidation using hypervalent iodineElectronic supplementary information (ESI) available. See DOI: 10.1039/c7sc02773g

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...

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Main Authors: Li, Guo-Xing, Morales-Rivera, Cristian A, Gao, Fang, Wang, Yaxin, He, Gang, Liu, Peng, Chen, Gong
Format: Article
Language:English
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Summary: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 H 2 O or CH 3 CN cosolvent is presented. We report a unified photoredox-catalysis strategy for both hydroxylation and amidation of tertiary and benzylic C-H bonds.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc02773g