Direct C-H Bond Arylation of (Hetero)arenes with Aryl and Heteroarylboronic Acids

被引：64

作者：

Guchhait, Sankar K. ^{[1
]}

Kashyap, Maneesh ^{[1
]}

Saraf, Shuddham ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Sector 67, Sas Nagar 160062, Punjab, India

来源：

SYNTHESIS-STUTTGART | 2010年 / 07期

关键词：

cross-coupling; direct arylation; biaryls; single-electron transfer; microwave; CATALYZED DIRECT ARYLATION; MANGANESE(III) ACETATE; COUPLING REACTION; ARENES; BIARYLS; FUNCTIONALIZATION; PHENYLHYDRAZINES; CYCLODEHYDRATION; PHOSPHONATION; HETEROARENES;

D O I：

10.1055/s-0029-1219234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel microwave-promoted protocol mediated by Mn(OAc)(3) was developed for the single-electron-transfer oxidative direct C-H bond arylation of (hetero)arenes with aryl and heteroarylboronic acids. Various electron-deactivated and electron-rich heteroarenes and benzene underwent successfully the direct arylation in this general process. The use of slight excess of heteroarene or benzene in this method was found to be sufficient.

引用

页码：1166 / 1170

页数：5

共 60 条

[1] Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations [J].

Ackermann, Lutz ;

Mulzer, Michael .

ORGANIC LETTERS, 2008, 10 (21) :5043-5045

[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] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].

Alonso, Francisco ;

Beletskaya, Irina P. ;

Yus, Miguel .

TETRAHEDRON, 2008, 64 (14) :3047-3101

[4] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, M. Mehdi ;

Naali, Fardin .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837

[5] Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].

Ban, Ikuya ;

Sudo, Tomoko ;

Taniguchi, Tadashi ;

Itami, Kenichiro .

ORGANIC LETTERS, 2008, 10 (16) :3607-3609

[6] Intramolecular direct arylation in the synthesis of fluorinated carbazoles [J].

Bedford, Robin B. ;

Betham, Michael ;

Charmant, Jonathan P. H. ;

Weeks, Amanda L. .

TETRAHEDRON, 2008, 64 (26) :6038-6050

[7] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[8] 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

[9] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[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 →