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

被引：112

作者：

Li, Guo-Xing ^{[1
,2
]}

Morales-Rivera, Cristian A. ^{[3
]}

Gao, Fang ^{[1
,2
]}

Wang, Yaxin ^{[1
,2
]}

He, Gang ^{[1
,2
]}

Liu, Peng ^{[3
]}

Chen, Gong ^{[1
,2
,4
]}

机构：

[1] Nankai Univ, State Key Lab, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

[3] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[4] Penn State Univ, Dept Chem, 104 Chem Bldg, University Pk, PA 16802 USA

来源：

CHEMICAL SCIENCE | 2017年 / 8卷 / 10期

基金：

美国国家科学基金会;

关键词：

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

D O I：

10.1039/c7sc02773g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：7180 / 7185

页数：6

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