Synthesis of 2,2′-Bipyridines via Suzuki-Miyaura Cross-Coupling

被引：28

作者：

Guetz, Christoph ^{[1
]}

Luetzen, Arne ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

SYNTHESIS-STUTTGART | 2010年 / 01期

关键词：

cross-coupling reactions; bipyridines; palladium; 2-pyridylboronic acid esters; Suzuki-Miyaura reaction; BIPYRIDINE; PYRIDINES; ESTERS; ACIDS;

D O I：

10.1055/s-0029-1217082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2'-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2'-bipyridines.

引用

页码：85 / 90

页数：6

共 50 条

[41] The Suzuki-Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization
Willemse, Tom
Schepens, Wim
van Vlijmen, Herman W. T.
Maes, Bert U. W.
Ballet, Steven
CATALYSTS, 2017, 7 (03)
[42] Reaction Optimization of a Suzuki-Miyaura Cross-Coupling Using Design of Experiments
Bobers, Jens
Hahn, Lisa Katharina
Averbeck, Tobias
Brunschweiger, Andreas
Kockmann, Norbert
CHEMIE INGENIEUR TECHNIK, 2022, 94 (05) : 780 - 785
[43] Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls
Braga, Ataualpa A. C.
Morgon, Nelson H.
Ujaque, Gregori
Lledos, Agusti
Maseras, Feliu
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (21) : 4459 - 4466
[44] Suzuki-Miyaura Cross-Coupling under Solvent-Free Conditions
Asachenko, Andrey F.
Sorochkina, Kristina R.
Dzhevakov, Pavel B.
Topchiy, Maxim A.
Nechaev, Mikhail S.
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3553 - 3557
[45] Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
Dreher, Spencer D.
Lim, Siang-Ee
Sandrock, Deidre L.
Molander, Gary A.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3626 - 3631
[46] New Tricyclic Aryl Quinazoline Derivatives by Suzuki-Miyaura Cross-Coupling
Elmuradov, Burkhon
Okmanov, Rasul
Juraev, Bakhromjon
Draeger, Gerald
Butenschoen, Holger
CHEMISTRYOPEN, 2024, 13 (12):
[47] Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
Blangetti, Marco
Rosso, Helena
Prandi, Cristina
Deagostino, Annamaria
Venturello, Paolo
MOLECULES, 2013, 18 (01) : 1188 - 1213
[48] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling in Continuous Flow
Len, Christophe
Bruniaux, Sophie
Delbecq, Frederic
Parmar, Virinder S.
CATALYSTS, 2017, 7 (05):
[49] Role of the Base and Control of Selectivity in the Suzuki-Miyaura Cross-Coupling Reaction
Lima, Carlos F. R. A. C.
Rodrigues, Ana S. M. C.
Silva, Vera L. M.
Silva, Artur M. S.
Santos, Luis M. N. B. F.
CHEMCATCHEM, 2014, 6 (05) : 1291 - 1302
[50] Highly practical boronic acid surrogates for the Suzuki-Miyaura cross-coupling
Bonin, Helene
Leuma-Yona, Rodrigue
Marchiori, Bruno
Demonchaux, Patrice
Gras, Emmanuel
TETRAHEDRON LETTERS, 2011, 52 (10) : 1132 - 1135

← 1 2 3 4 5 →