Selective Oxidation of Benzylic C-H Bonds Catalyzed by Cu(II)/{PMo12}

被引:33
作者
Li, Peihe [1 ]
Wang, Yingying [1 ]
Wang, Xia [1 ]
Wang, Yin [1 ]
Liu, Ying [1 ]
Huang, Keke [3 ]
Hu, Jing [1 ]
Duan, Limei [1 ]
Hu, Changwen [2 ]
Liu, Jinghai [1 ]
机构
[1] Inner Mongolia Univ Nationalities, Coll Chem & Mat Sci, NII, Inner Mongolia Key Lab Carbon Nanomat, Tongliao 028000, Peoples R China
[2] Beijing Inst Technol, Sch Chem & Chem Engn, Beijing Key Lab Photoelect Electrophoton, Minist Educ,Key Lab Cluster Sci, Beijing 100081, Peoples R China
[3] Jilin Univ, Coll Chem, State Key Lab Inorgan Synth & Preparat Chem, Changchun 130012, Peoples R China
基金
中国国家自然科学基金;
关键词
AEROBIC OXIDATION; EFFICIENT; POLYOXOMETALATE; HYDROCARBONS; TERT; OXYGENATION; ALKYLARENES; ACTIVATION; ETHYLBENZENE; COMPLEXES;
D O I
10.1021/acs.joc.9b02997
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Precise catalytic regulation of carbon radical generation by a highly active oxygen radical to abstract the H atom in a C-H bond is an effective method for the selective activation of C-H synthetic chemistry. Herein, we report a facile catalyst system with commercially available copper(II)/{PMo12} to form a tert-butanol radical intermediate for the selective oxidation of benzylic C-H bonds. The reaction shows a broad range of substrates (benzyl methylene, benzyl alcohols) with good functional group tolerance and chemical selectivity. The corresponding carbonyl compounds were synthesized with good yields under mild conditions. DFT calculations and experimental analysis further demonstrated a reasonable carbon radical mechanism for this type of organic transformation reaction.
引用
收藏
页码:3101 / 3109
页数:9
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