Cross-coupling of aromatic esters and amides

被引:410
作者
Takise, Ryosuke [1 ]
Muto, Kei [2 ]
Yamaguchi, Junichiro [2 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Waseda Univ, Dept Appl Chem, Shinjuku Ku, 3-4-1 Ohkubo, Tokyo 1698555, Japan
关键词
REDOX-ACTIVE ESTERS; N-C CLEAVAGE; CATALYZED DECARBONYLATIVE BORYLATION; H BOND FUNCTIONALIZATION; ACYL-OXYGEN BONDS; KETONE SYNTHESIS; ARYL ESTERS; ACID-CHLORIDES; THIOPEPTIDE ANTIBIOTICS; ORGANOBORON COMPOUNDS;
D O I
10.1039/c7cs00182g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic cross-coupling reactions of aromatic esters and amides have recently gained considerable attention from synthetic chemists as de novo and efficient synthetic methods to form C-C and C-heteroatom bonds. Esters and amides can be used as diversifiable groups in metal-catalyzed cross-coupling: in a decarbonylative manner, they can be utilized as leaving groups, whereas in a non-decarbonylative manner, they can form ketone derivatives. In this review, recent advances of this research topic are discussed.
引用
收藏
页码:5864 / 5888
页数:25
相关论文
共 149 条
[11]   DECARBONYLATION OF AROMATIC CARBONYL COMPOUNDS CATALYZED BY RHODIUM COMPLEXES [J].
BLUM, J ;
OPPENHEIMER, E ;
BERGMANN, ED .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2338-+
[12]   ALUMINUM CHLORIDE-PROMOTED TRANSAMIDATION REACTIONS [J].
BON, E ;
BIGG, DCH ;
BERTRAND, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4035-4036
[13]   The ruthenium-catalyzed reductive decarboxylation of esters: Catalytic reactions involving the cleavage of acyl-oxygen bonds of esters [J].
Chatani, N ;
Tatamidani, H ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4849-4850
[14]   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
[15]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[16]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[17]   Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A [J].
Coqueron, PY ;
Didier, C ;
Ciufolini, MA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) :1411-1414
[18]   Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters [J].
Cornella, Josep ;
Edwards, Jacob T. ;
Qin, Tian ;
Kawamura, Shuhei ;
Wang, Jie ;
Pan, Chung-Mao ;
Gianatassio, Ryan ;
Schmidt, Michael ;
Eastgate, Martin D. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (07) :2174-2177
[19]   Nickel-Catalyzed Decarbonylative C-H Coupling Reactions: A Strategy for Preparing Bis(heteroaryl) Backbones [J].
Correa, Arkaitz ;
Cornella, Josep ;
Martin, Ruben .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :1878-1880
[20]   Breaking Amides using Nickel Catalysis [J].
Dander, Jacob E. ;
Garg, Neil K. .
ACS CATALYSIS, 2017, 7 (02) :1413-1423