Copper-/Silver-Mediated Arylation of C(sp2)-H Bonds with 2-Thiophenecarboxylic Acids

被引：66

作者：

Zhao, Sheng ^{[1
]}

Liu, Yue-Jin ^{[1
]}

Yan, Sheng-Yi ^{[1
]}

Chen, Fa-Jie ^{[1
]}

Zhang, Zhuo-Zhuo ^{[1
]}

Shi, Bing-Feng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 13期

关键词：

C-H BONDS; CATALYZED DECARBOXYLATIVE ARYLATION; CARBOXYLIC-ACIDS; UNACTIVATED C(SP(3))-H; ORTHO-HALOGENATION; COUPLING REACTIONS; BENZOIC-ACIDS; PALLADIUM; ARENES; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.5b01560

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper/silver-mediated arylation of (hetero)aryl C-H bonds with 2-thiophenecarboxylic acids has been achieved. The protocol features a broad substrate scope and high functional group tolerance. Preliminary mechanistic studies indicate that a cascade protodecarboxylation/dehydrogenative coupling process is likely involved.

引用

页码：3338 / 3341

页数：4

共 69 条

[1] 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

[2]

[Anonymous], 2015, ACCOUNTS CHEM RES

[3] New approaches for decarboxylative biaryl coupling [J].

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375

[4] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].

Becht, Jean-Michel ;

Catala, Cedric ;

Le Drian, Claude ;

Wagner, Alain .

ORGANIC LETTERS, 2007, 9 (09) :1781-1783

[5] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[6] Cu(II)-Mediated C-S/N-S Bond Formation via C-H Activation: Access to Benzoisothiazolones Using Elemental Sulfur [J].

Chen, Fa-Jie ;

Liao, Gang ;

Li, Xin ;

Wu, Jun ;

Shi, Bing-Feng .

ORGANIC LETTERS, 2014, 16 (21) :5644-5647

[7] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].

Chen, Fa-Jie ;

Zhao, Sheng ;

Hu, Fang ;

Chen, Kai ;

Zhang, Qi ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192

[8] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[9] Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives [J].

Chen, Xiao ;

Dobereiner, Graham ;

Hao, Xue-Shi ;

Giri, Ramesh ;

Maugel, Nathan ;

Yu, Jin-Quan .

TETRAHEDRON, 2009, 65 (16) :3085-3089

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

Cornella, Josep ;

Larrosa, Igor .

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

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