A practical and general synthesis of unsymmetrical terphenyls

被引：78

作者：

Antelo Miguez, Jose M.

Angel Adrio, Luis

Sousa-Pedrares, Antonio

Vila, Jose M.

Hii, King Kuok

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, Kensington SW7 2AZ, England

[2] Univ Santiago de Compostela, Fac Quim, Dept Quim Inorgan, E-15782 Santiago De Compostela, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 20期

关键词：

D O I：

10.1021/jo701308b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.

引用

收藏

页码：7771 / 7774

页数：4

相关论文

共 34 条

[1] A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants [J].

Arcadi, A ;

Cerichelli, G ;

Chiarini, M ;

Correa, M ;

Zorzan, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) :4080-4086

[2] Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].

Arvela, RK ;

Leadbeater, NE .

ORGANIC LETTERS, 2005, 7 (11) :2101-2104

[3] Non-trivial behavior of palladium(II) acetate [J].

Bakhmutov, VI ;

Berry, JF ;

Cotton, FA ;

Ibragimov, S ;

Murillo, CA .

DALTON TRANSACTIONS, 2005, (11) :1989-1992

[4] MOLECULAR-DYNAMICS SIMULATION STUDY OF SOLID POLYPHENYLS - STRUCTURES DETERMINED BY THE INTERPLAY BETWEEN INTRAMOLECULAR AND INTERMOLECULAR FORCES [J].

BARANYAI, A ;

WELBERRY, TR .

MOLECULAR PHYSICS, 1992, 75 (04) :867-879

[5] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[6] Successive replacement of halogen atoms in 4,6-dihaloquinolines in cross-coupling reactions with arylboronic acids catalyzed by palladium and nickel complexes [J].

Beletskaya, IP ;

Tsvetkov, AV ;

Latyshev, GV ;

Lukashev, NV .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (11) :1660-1667

[7] Taking too many precautions in making a catalyst is never a loss of time: A lesson we learned at our own expense [J].

Bianchini, C ;

Meli, A ;

Oberhauser, W .

ORGANOMETALLICS, 2003, 22 (21) :4281-4285

[8] Direct C-H arylation of purines:: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

ORGANIC LETTERS, 2006, 8 (23) :5389-5392

[9] Carbohydrate rod conjugates: Ternary rod-coil molecules forming complex liquid crystal structures\ [J].

Chen, B ;

Baumeister, U ;

Pelzl, G ;

Das, MK ;

Zeng, XB ;

Ungar, G ;

Tschierske, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16578-16591

[10] Preparation of unsymmetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents [J].

Cho, CH ;

Kim, IS ;

Park, KY .

TETRAHEDRON, 2004, 60 (21) :4589-4599

← 1 2 3 4 →