Electrochemical Cobalt-Catalyzed C-H Oxygenation at Room Temperature

被引:280
作者
Sauermann, Nicolas [1 ]
Meyer, Tjark H. [1 ]
Tian, Cong [1 ]
Ackermann, Lutz [1 ]
机构
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
关键词
CROSS-COUPLING REACTIONS; CARBON-HYDROGEN; MECHANISTIC INSIGHTS; BOND FORMATION; PALLADIUM; FUNCTIONALIZATION; METAL; OXIDATION; ARYLATION; ACTIVATION;
D O I
10.1021/jacs.7b11025
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electrochemical cobalt-catalyzed C-H functionalizations were achieved in terms of C-H oxygenation under mild conditions at 23 degrees C. The robust electrochemical C-H functionalization was characterized by ample substrate scope, whereas mechanistic studies provided support for a facile C-H cleavage. The electrochemical cobalt-catalyzed C-H oxygenation proved viable on arenes and alkenes with excellent levels of positional and diastereo-selectivity, avoiding the use of stoichiometric silver(I) oxidants under ambient conditions.
引用
收藏
页码:18452 / 18455
页数:4
相关论文
共 71 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[3]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[4]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[5]   Catalytic Electrochemical C-H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current [J].
Aiso, Hiroko ;
Kochi, Takuya ;
Mutsutani, Hitoshi ;
Tanabe, Takamasa ;
Nishiyama, Shigeru ;
Kakiuchi, Fumitoshi .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7718-7724
[6]   Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes [J].
Amatore, Christian ;
Cammoun, Chama ;
Jutand, Anny .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :292-296
[7]   Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators [J].
Badalyan, Artavazd ;
Stahl, Shannon S. .
NATURE, 2016, 535 (7612) :406-410
[8]   Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions [J].
Castro, Luis C. Misal ;
Chatani, Naoto .
CHEMISTRY LETTERS, 2015, 44 (04) :410-421
[9]   Iron-Catalyzed C-H Functionalization Processes [J].
Cera, Gianpiero ;
Ackermann, Lutz .
TOPICS IN CURRENT CHEMISTRY, 2016, 374 (05)
[10]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115