A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine. Issue 10 (8th September 2017)

• Record Type: Journal Article
• Authors: Li, Guo-Xing; Morales-Rivera, Cristian A.; Gao, Fang; Wang, Yaxin; He, Gang; Liu, Peng; Chen, Gong
• Is Part Of: Chemical science. Volume 8:Issue 10(2017)
• Page Start: 7180
• Page End: 7185
• Publication Date: 2017-09-08
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc02773g
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We report a unified photoredox-catalysis strategy for both hydroxylation and amidation of tertiary and benzylic C–H bonds. 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 H2 O or CH3 CN cosolvent is presented.