Palladium-Catalyzed Oxidative Arylation of Tertiary Benzamides: Para-Selectivity of Monosuhstituted Arenes

被引：42

作者：

Yang, Ze ^{[1
]}

Qiu, Fang-Cheng ^{[1
]}

Gao, Juan ^{[1
]}

Li, Zeng-Wen ^{[1
]}

Guan, Bing-Tao ^{[1
,2
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, State Key Lab & Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 17期

关键词：

C-H ACTIVATION; ARYL BOND FORMATION; COUPLING REACTIONS; FUNCTIONALIZATION; ALKENYLATION; RHODIUM(III); OLEFINATION; C(SP(2))-H; ANILIDES; ALKYNES;

D O I：

10.1021/acs.orglett.5b02135

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient protocol for the high para-selective arylation of monosubstituted arenes with tertiary benzamides has been developed via palladium-catalyzed oxidative coupling reactions. Due to the mild conditions and the easy availability of substrates and oxidant, this method could potentially provide a practical approach for the synthesis of para-substituted biaryl compounds.

引用

页码：4316 / 4319

页数：4

共 58 条

[1] Arene C-H bond activation and arene oxidative coupling by cationic palladium(II) complexes [J].

Ackerman, LJ ;

Sadighi, JP ;

Kurtz, DM ;

Labinger, JA ;

Bercaw, JE .

ORGANOMETALLICS, 2003, 22 (19) :3884-3890

[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] Intermolecular oxidative cross-coupling of arenes [J].

Ashenhurst, James A. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548

[4] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].

BEAK, P ;

SNIECKUS, V .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312

[5] Cyclopalladation of N-phenylbenzamides: Synthesis and structure of bimetallic palladium(II)-complexes [J].

Borduas, Nadine ;

Lough, Alan J. ;

Dong, Vy M. .

INORGANICA CHIMICA ACTA, 2011, 369 (01) :247-252

[6] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].

Brasche, Gordon ;

Garcia-Fortanet, Jorge ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (11) :2207-2210

[7] Palladium-Catalyzed Selective Dehydrogenative Cross-Couplings of Heteroarenes [J].

Bugaut, Xavier ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7479-7481

[8] Computational Study of Intramolecular Arene Palladation at a Palladium(IV) Center [J].

Canty, Allan J. ;

Ariafard, Alireza ;

Yates, Brian F. ;

Sanford, Melanie S. .

ORGANOMETALLICS, 2015, 34 (06) :1085-1090

[9] 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

[10] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

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