Pd(II)-Catalyzed arylation of unactivated methylene C(sp3)-H bonds with aryl halides using a removable auxiliary

被引：81

作者：

Zhang, Qi ^{[1
]}

Yin, Xue-Song ^{[1
]}

Zhao, Sheng ^{[1
]}

Fang, Sheng-Long ^{[1
]}

Shi, Bing-Feng ^{[1
,2
]}

机构：

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

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 61期

基金：

美国国家科学基金会;

关键词：

C-H BONDS; CATALYZED DIRECT ARYLATION; CARBON-HYDROGEN BONDS; COUPLING REACTIONS; DIRECTING GROUP; BETA-LACTAMS; PALLADIUM; FUNCTIONALIZATION; ACTIVATION; ALKYLATION;

D O I：

10.1039/c4cc03615h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd(II)-catalyzed arylation of methylene C(sp(3))-H bonds in aliphatic amides directed by our newly developed PIP directing group with aryl iodides/bromides has been achieved. Arylation occurs efficiently with a broad range of aryl halides and amides.

引用

页码：8353 / 8355

页数：3

共 60 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[3] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901

[4] 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

[5]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[6] Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds [J].

Aspin, Sam ;

Goutierre, Anne-Sophie ;

Larini, Paolo ;

Jazzar, Rodolphe ;

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10808-10811

[7] The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].

Baudoin, O ;

Herrbach, A ;

Guéritte, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740

[8] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[9] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[10] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

← 1 2 3 4 5 6 →