Decarbonylative Reductive Coupling of Aromatic Esters by Nickel and Palladium Catalyst

被引：5

作者：

Peng, Yunfei ^{[1
]}

Isshiki, Ryota ^{[1
]}

Muto, Kei ^{[2
]}

Yamaguchi, Junichiro ^{[1
]}

机构：

[1] Waseda Univ, Dept Appl Chem, Shinjuku Ku, 513 Wasedatsurumakicho, Tokyo 1620041, Japan

[2] Waseda Univ, Waseda Inst Adv Study, Shinjuku Ku, 513 Wasedatsurumakicho, Tokyo 1620041, Japan

来源：

CHEMISTRY LETTERS | 2022年 / 51卷 / 07期

关键词：

Decarbonylative reaction; Reductive coupling; Biaryls; ARYL BOND FORMATION; BIARYL COMPOUNDS; ALPHA-ARYLATION; C-O; PD; INTERCONVERSION; OLEFINATION; SILYLATION; CHEMISTRY; KETONES;

D O I：

10.1246/cl.220214

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ni or Pd-catalyzed decarbonylative reductive couplings of aromatic esters were developed. A range of (hetero)aromatic esters was applicable to these reductive homocoupling reactions. Moreover, it was found that Pd-catalysis enables a reductive decarbonylative cross-coupling between two different aromatic esters to afford a nonsymmetrical biaryls system.

引用

页码：749 / 753

页数：5

共 77 条

[1] Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates [J].

Ackerman, Laura K. G. ;

Lovell, Matthew M. ;

Weix, Daniel J. .

NATURE, 2015, 524 (7566) :454-+

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy [J].

Amaike, Kazuma ;

Itami, Kenichiro ;

Yamaguchi, Junichiro .

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 [J].

Amaike, Kazuma ;

Muto, Kei ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576

[5] 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

[6] Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis [J].

Cao, Zhi-Chao ;

Luo, Qin-Yu ;

Shi, Zhang-Jie .

ORGANIC LETTERS, 2016, 18 (23) :5978-5981

[7] Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings [J].

Chatupheeraphat, Adisak ;

Liao, Hsuan-Hung ;

Srimontree, Watchara ;

Guo, Lin ;

Minenkov, Yury ;

Poater, Albert ;

Cavallo, Luigi ;

Rueping, Magnus .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) :3724-3735

[8] Nickel-Catalyzed C-CN Bond Formation via Decarbonylative Cyanation of Esters, Amides, and Intramolecular Recombination Fragment Coupling of Acyl Cyanides [J].

Chatupheeraphat, Adisak ;

Liao, Hsuan-Hung ;

Lee, Shao-Chi ;

Rueping, Magnus .

ORGANIC LETTERS, 2017, 19 (16) :4255-4258

[9] Decarboxylative Carbon-Carbon Bond-Forming Transformations of (Hetero)aromatic Carboxylic Acids [J].

Cornella, Josep ;

Larrosa, Igor .

SYNTHESIS-STUTTGART, 2012, 44 (05) :653-676

[10] Decarboxylative homocoupling of (hetero) aromatic carboxylic acids [J].

Cornella, Josep ;

Lahlali, Hicham ;

Larrosa, Igor .

CHEMICAL COMMUNICATIONS, 2010, 46 (43) :8276-8278

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