Cobalt-Catalyzed Esterification of Amides

被引:96
作者
Bourne-Branchu, Yann [1 ]
Gosmini, Corinne [1 ]
Danoun, Gregory [1 ]
机构
[1] Univ Paris Saclay, CNRS, Ecole Polytech, LCM, F-91128 Palaiseau, France
关键词
amides; cobalt; cross-coupling; esterification; homogeneous catalysis; N-C CLEAVAGE; CHEMOSELECTIVE KETONE SYNTHESIS; CROSS-COUPLING REACTIONS; CARBON-CARBON BONDS; TWISTED AMIDES; TERTIARY AMIDE; GENERAL-METHOD; ACTIVATION; FUNCTIONALIZATION; TRANSAMIDATION;
D O I
10.1002/chem.201702608
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first cobalt-catalyzed amide activation of N-Boc-amides, and their conversion into esters, is reported here. This new methodology presents a very practical process that does not require an inert atmosphere, uses an inexpensive cobalt catalyst, and proceeds under mild reaction conditions. This catalytic system has a broad substrate scope and has been shown to be highly efficient, with catalyst loadings as low as 1 mol%.
引用
收藏
页码:10043 / 10047
页数:5
相关论文
共 95 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]  
Amatore M., 2008, ANGEW CHEM, V120, P2119
[3]   Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate [J].
Amatore, Muriel ;
Gosmini, Corinne .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2089-2092
[4]  
[Anonymous], 2015, ANGEW CHEM, DOI [DOI 10.1002/ANGE.201507776, 10.1002/ange.201507776]
[5]  
[Anonymous], 2015, ANGEW CHE
[6]  
[Anonymous], 2016, ANGEW CHEM
[7]  
[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451
[8]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[9]   A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis [J].
Baker, Emma L. ;
Yamano, Michael M. ;
Zhou, Yujing ;
Anthony, Sarah M. ;
Garg, Neil K. .
NATURE COMMUNICATIONS, 2016, 7
[10]  
Brchmer M.C., 2011, Angew. Chem, V123, P6299