Cross-coupling of aromatic esters and amides

被引:403
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
    BLUM, J
    OPPENHEIMER, E
    BERGMANN, ED
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) : 2338 - +
  • [12] ALUMINUM CHLORIDE-PROMOTED TRANSAMIDATION REACTIONS
    BON, E
    BIGG, DCH
    BERTRAND, G
    [J]. 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
    Chatani, N
    Tatamidani, H
    Ie, Y
    Kakiuchi, F
    Murai, S
    [J]. 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
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [15] The sonogashira reaction:: A booming methodology in synthetic organic chemistry
    Chinchilla, Rafael
    Najera, Carmen
    [J]. CHEMICAL REVIEWS, 2007, 107 (03) : 874 - 922
  • [16] Recent advances in Sonogashira reactions
    Chinchilla, Rafael
    Najera, Carmen
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5084 - 5121
  • [17] Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A
    Coqueron, PY
    Didier, C
    Ciufolini, MA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) : 1411 - 1414
  • [18] Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters
    Cornella, Josep
    Edwards, Jacob T.
    Qin, Tian
    Kawamura, Shuhei
    Wang, Jie
    Pan, Chung-Mao
    Gianatassio, Ryan
    Schmidt, Michael
    Eastgate, Martin D.
    Baran, Phil S.
    [J]. 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
    Correa, Arkaitz
    Cornella, Josep
    Martin, Ruben
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) : 1878 - 1880
  • [20] Breaking Amides using Nickel Catalysis
    Dander, Jacob E.
    Garg, Neil K.
    [J]. ACS CATALYSIS, 2017, 7 (02): : 1413 - 1423