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

来源：

CHEMICAL SOCIETY REVIEWS | 2017年 / 46卷 / 19期

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

页码：5864 / 5888

页数：25

共 149 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
Ackermann, Lutz
Vicente, Ruben
Kapdi, Anant R.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[3] Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy
Amaike, Kazuma
Itami, Kenichiro
Yamaguchi, Junichiro
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (13) : 4384 - 4388
[4] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
Amaike, Kazuma
Muto, Kei
Yamaguchi, Junichiro
Itami, Kenichiro
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13573 - 13576
[5] A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis
Baker, Emma L.
Yamano, Michael M.
Zhou, Yujing
Anthony, Sarah M.
Garg, Neil K.
[J]. NATURE COMMUNICATIONS, 2016, 7
[6] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[7] A Cross-Coupling Approach to Amide Bond Formation from Esters
Ben Halima, Taoufik
Vandavasi, Jaya Kishore
Shkoor, Mohanad
Newman, Stephen G.
[J]. ACS CATALYSIS, 2017, 7 (03): : 2176 - 2180
[8] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
Ben Halima, Taoufik
Zhang, Wanying
Yalaoui, Imane
Hong, Xin
Yang, Yun-Fang
Houk, Kendall N.
Newman, Stephen G.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1311 - 1318
[9] The first Suzuki cross-couplings of aryltrimethylammonium salts
Blakey, SB
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) : 6046 - 6047
[10] THE PALLADIUM-CATALYZED ARYLATION OF ACTIVATED ALKENES WITH AROYL CHLORIDES
BLASER, HU
SPENCER, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 233 (02) : 267 - 274

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