A unified photoredox-catalysis strategy for C(sp3)–
H hydroxylation and amidation using hypervalent
iodine
Guo-Xing Li,a Cristian A. Morales-Rivera,b Fang Gao,a Yaxin Wang,a Gang He,a
Peng Liu
*b and Gong Chen
*ac
aState Key Laboratory and Institute of Elemento-Organic Chemistry, College of
Chemistry, Collaborative Innovation Center of Chemical Science and Engineering
(Tianjin), Nankai University, Tianjin 300071, China. E-mail: gongchen@nankai.edu.
cn
bDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. E-mail: pengliu@pitt.edu
cDepartment of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, USA. E-mail: guc11@psu.edu
bDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. E-mail: pengliu@pitt.edu
cDepartment of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, USA. E-mail: guc11@psu.edu
Chem. Sci. 2017, ASAP
DOI: 10.1039/c7sc02773g
http://pubs.rsc.org/en/content/articlepdf/2017/sc/c7sc02773g?page=search
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.
