Cp*CoIII-Catalyzed C(sp3)-H Bond Amidation of 8-Methylquinoline

被引:128
作者
Barsu, Nagaraju [1 ]
Rahman, Md Atiur [1 ]
Sen, Malay [1 ]
Sundararaju, Basker [1 ]
机构
[1] Indian Inst Technol Kanpur, Dept Chem, Fine Chem Lab, Kanpur 208016, Uttar Pradesh, India
关键词
amidation; cobalt; quinoline; sp(3) C-H activation; H AMIDATION; INTERMOLECULAR AMIDATION; COBALT(III)-CATALYZED ARYL; INDOLE SYNTHESIS; CARBON-CARBON; C-SP3-H BONDS; ACTIVATION; FUNCTIONALIZATION; AMINATION; ALKYNES;
D O I
10.1002/chem.201601597
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and external oxidant-free, Cp*Co-III-catalyzed C(sp(3))-H bond amidation of 8-methylquinoline, using oxazolone as an efficient amidating agent, is reported for the first time under mild conditions. The reaction is selective and tolerates a variety of functional groups. Based on previous reports and experimental results, the deprotonation pathway proceeds through an external base-assisted concerted metalation and deprotonation process.
引用
收藏
页码:9135 / 9138
页数:4
相关论文
共 104 条
[1]   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
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]  
[Anonymous], 2015, ANGEW CHEM
[4]  
[Anonymous], 2013, ANGEW CHEM-GER EDIT
[5]  
[Anonymous], 2015, Angew. Chem.
[6]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[7]   Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer [J].
Barsu, Nagaraju ;
Sen, Malay ;
Premkumar, J. Richard ;
Sundararaju, Basker .
CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1338-1341
[8]   Carboxylate Assisted Ni-Catalyzed CH Bond Allylation of Benzamides [J].
Barsu, Nagaraju ;
Kalsi, Deepti ;
Sundararaju, Basker .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (26) :9364-9368
[9]  
Bizet V., 2014, ANGEW CHEM, V126, P5745, DOI 10.1002/ange.201310790
[10]   Sulfur Imidations by Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions [J].
Bizet, Vincent ;
Bolm, Carsten .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (13) :2854-2860