A unified photoredox-catalysis strategy for C(sp(3))-H hydroxylation and amidation using hypervalent iodine

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

来源：Chemical Science, 2017, 8(10): 7180-7185.

DOI：10.1039/c7sc02773g

• C-H BONDS
• TRANSITION-METAL-COMPLEXES
• UNACTIVATED C-SP3-H BONDS
• OXIDATION
• AMINATION
• EFFICIENT
• FUNCTIONALIZATION
• POTENTIALS
• GENERATION
• CHEMISTRY

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.

• 出版日期2017-10-1
• 单位南开大学