Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium Catalyzed C-H Bond Functionalization Methodology

被引：12

作者：

Kwak, Se Hun ^{[1
]}

Gulia, Nurbey ^{[1
,2
]}

Daugulis, Olafs ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

[2] Univ Wroclaw, Dept Chem, 14 F Joliot Curie, PL-50383 Wroclaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 10期

关键词：

ANILIDE ORTHO-ARYLATION; DIARYLIODONIUM SALTS; DIRECTING GROUP; ARYL CHLORIDES; BORONIC ACIDS; ACTIVATION; ETHYLENE; COPOLYMERIZATION; PHENANTHRIDINES; CARBOXYLATE;

D O I：

10.1021/acs.joc.8b00659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,5-Dimethylpyrazole was employed as a mono-d entate directing group for palladium-catalyzed ortho-sp(2) C-H arylation with aryl iodides. The reaction shows good functional group tolerance and outstanding selectivity for mono-orthoarylation. Ozonolysis of ortho-arylated arylpyrazoles gave acylated biphenylamines that were further arylated to afford unsymmetrically substituted 2,6-diarylacetanilides.

引用

收藏

页码：5844 / 5850

页数：7

相关论文

共 43 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].

Ackermann, L ;

Althammer, A ;

Born, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622

[2] Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water [J].

Ackermann, Lutz ;

Pospech, Jola ;

Potukuchi, Harish Kumar .

ORGANIC LETTERS, 2012, 14 (08) :2146-2149

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

Ackermann, Lutz .

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

[4] C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems [J].

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6629-6632

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

Baudoin, Olivier .

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

[6] Room-Temperature Synthesis of Pyrazoles, Diazepines, β-Enaminones, and β-Enamino Esters Using Silica-Supported Sulfuric Acid as a Reusable Catalyst Under Solvent-Free Conditions [J].

Chen, Xiang ;

She, Jin ;

Shang, Zhi-Cai ;

Wu, Jun ;

Zhang, Peizhi .

SYNTHETIC COMMUNICATIONS, 2009, 39 (06) :947-957

[7] Mechanistic Studies of Pd(II)-Catalyzed Copolymerization of Ethylene and Vinylalkoxysilanes: Evidence for a β-Silyl Elimination Chain Transfer Mechanism [J].

Chen, Zhou ;

Liu, Weijun ;

Daugulis, Olafs ;

Brookhart, Maurice .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) :16120-16129

[8] Ruthenium-catalyzed ortho-arylation of acetanilides with aromatic boronic acids: an easy route to prepare phenanthridines and carbazoles [J].

Chinnagolla, Ravi Kiran ;

Jeganmohan, Masilamani .

CHEMICAL COMMUNICATIONS, 2014, 50 (19) :2442-2444

[9] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[10] Mild conditions for copper-catalysed N-arylation of pyrazoles [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709

← 1 2 3 4 5 →