Base-Controlled One-Pot Chemoselective Suzuki-Miyaura Reactions for the Synthesis of Unsymmetrical Terphenyls

被引：3

作者：

Li, Xinmin ^{[1
]}

Feng, Fangfang ^{[1
]}

Ren, Changyue ^{[1
]}

Teng, Yong ^{[1
]}

Hu, Qinghong ^{[1
]}

Yuan, Zeli ^{[1
]}

机构：

[1] Zunyi Med Univ, Sch Pharm, Zunyi 563000, Guizhou, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 19期

关键词：

chemoselective; Suzuki-Miyaura reactions; unsymmetrical terphenyls; one-pot; ligand-free; CROSS-COUPLING REACTIONS; DERIVATIVES; PYRIDINES; SUFEX;

D O I：

10.1055/s-0039-1690227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a chemoselective Suzuki-Miyaura reaction protocol of using bromophenyl fluorosulfonate as building block for the preparation of unsymmetrical terphenyls. The chemoselective cross-coupling of bromophenyl fluorosulfonate and arylboronic acids can be achieved by controlling base species without using any ligands. Under this methodology, various of m- and p-unsymmetrical terphenyls were obtained in moderate to good yields.

引用

页码：2131 / 2135

页数：5

共 40 条

[1] A practical and general synthesis of unsymmetrical terphenyls [J].

Antelo Miguez, Jose M. ;

Angel Adrio, Luis ;

Sousa-Pedrares, Antonio ;

Vila, Jose M. ;

Hii, King Kuok .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7771-7774

[2] Self-Assembly of Mono- And Bidentate Oligoarylene Thiols onto Polycrystalline Au [J].

Casallini, S. ;

Berto, M. ;

Leonardi, F. ;

Operamolla, A. ;

Bortolotti, C. A. ;

Borsari, M. ;

Sun, W. ;

Di Felice, R. ;

Corni, S. ;

Albonetti, C. ;

Hassan Omar, O. ;

Farinola, G. M. ;

Biscarini, F. .

LANGMUIR, 2013, 29 (43) :13198-13208

[3] One-pot synthesis of multisubstituted quaterphenyls and cyclopropanes [J].

Chang, Meng-Yang ;

Chan, Chieh-Kai ;

Lin, Shin-Ying ;

Wu, Ming-Hao .

TETRAHEDRON, 2013, 69 (47) :10036-10044

[4] One-pot synthesis of functionalized p-terphenyl derivatives [J].

Chang, Meng-Yang ;

Chan, Chieh-Kai ;

Wu, Ming-Hao .

TETRAHEDRON, 2013, 69 (37) :7916-7924

[5]

Cho C. H., 2010, EUR J ORG CHEM, V2005, P3177

[6] Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry [J].

Dong, Jiajia ;

Krasnova, Larissa ;

Finn, M. G. ;

Sharpless, K. Barry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9430-9448

[7] Chemoselective Suzuki-Miyaura Cross-Coupling via Kinetic Transmetallation [J].

Fyfe, James W. B. ;

Fazakerley, Neal J. ;

Watson, Allan J. B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (05) :1249-1253

[8] Gold-Catalyzed Cycloaromatization of 2,4-Dien-6-yne Carboxylic Acids: Synthesis of 2,3-Disubstituted Phenols and Unsymmetrical Bi- and Terphenyls [J].

Garcia-Garcia, Patricia ;

Fernandez-Rodriguez, Manuel A. ;

Aguilar, Enrique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) :5534-5537

[9] A simple and modular strategy for small molecule synthesis: Iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks [J].

Gillis, Eric P. ;

Burke, Martin D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6716-+

[10] A vicarious synthesis of unsymmetrical meta- and para-terphenyls from 2H-pyran-2-ones [J].

Goel, A ;

Verma, D ;

Singh, FV .

TETRAHEDRON LETTERS, 2005, 46 (49) :8487-8491

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