A novel zinc-catalyzed Suzuki-type cross-coupling reaction of aryl boronic acids with alkynyl bromides

被引：25

作者：

Krishnan, K. Keerthi ^{[1
]}

Saranya, Salim ^{[1
]}

Rohit, K. R. ^{[1
]}

Anilkumar, Gopinathan ^{[1
]}

机构：

[1] Mahatma Gandhi Univ, Sch Chem Sci, PD Hills PO, Kottayam 686560, Kerala, India

来源：

JOURNAL OF CATALYSIS | 2019年 / 372卷

关键词：

Zinc catalysis; Suzuki coupling; Cross-coupling; Boronic acids; Bromides; TERMINAL ALKYNES; SONOGASHIRA; PERSPECTIVES; IODIDES; HALIDES; PROTOCOL; COMPLEXES; WATER;

D O I：

10.1016/j.jcat.2019.03.005

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A novel Suzuki-type cross-coupling reaction of organoboron reagents with alkynyl bromides has been developed in the presence of catalytic Et2Zn/DMEDA system. The reaction afforded a variety of internal alkynes in moderate to excellent yields under mild reaction conditions without the formation of any homo-coupling products. The resulting internal alkynes have valuable applications in pharmaceutical and industrial areas. The use of relatively non-toxic zinc, chelating amine ligand and low reaction temperature make this protocol an alternative for the synthesis of internal alkynes. The scope and limitations of this protocol are also investigated. (C) 2019 Elsevier Inc. All rights reserved.

引用

页码：266 / 271

页数：6

共 45 条

[11] Recent advances in the transition metal catalyzed etherification reactions
Krishnan, K. Keerthi
Ujwaldev, Sankuviruthiyil M.
Sindhu, Kallikkakam S.
Anilkumar, Gopinathan
[J]. TETRAHEDRON, 2016, 72 (47) : 7393 - 7407
[12] Recent advances and perspectives in the manganese-catalysed epoxidation reactions
Krishnan, K. Keerthi
Thomas, Anns Maria
Sindhu, Kallikkakam S.
Anilkumar, Gopinathan
[J]. TETRAHEDRON, 2016, 72 (01) : 1 - 16
[13] A versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles
Kudo, N
Perseghini, M
Fu, GC
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) : 1282 - 1284
[14] Recent Developments in the Suzuki-Miyaura Reaction: 2010-2014
Maluenda, Irene
Navarro, Oscar
[J]. MOLECULES, 2015, 20 (05): : 7528 - 7557
[15] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
Martin, Ruben
Buchwald, Stephen L.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1461 - 1473
[16] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483
[17] Efficient ligandless palladium-catalyzed Suzuki reactions of potassium aryltrifluoroborates
Molander, GA
Biolatto, B
[J]. ORGANIC LETTERS, 2002, 4 (11) : 1867 - 1870
[18] Formation of carbon-carbon bonds under catalysis by transition-metal nanoparticles
Moreno-Mañas, M
Pleixats, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (08) : 638 - 643
[19] A Zinc Catalyzed C(sp3)-C(sp2) Suzuki-Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates
Procter, Richard J.
Dunsford, Jay J.
Rushworth, Philip J.
Hulcoop, David G.
Layfield, Richard A.
Ingleson, Michael J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (63) : 15889 - 15893
[20] Recent Developments and Perspectives in the Zinc-Catalysed Michael Addition
Rohit, K. R.
Ujwaldev, S. M.
Krishnan, K. Keerthi
Anilkumar, Gopinathan
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 85 - 102

← 1 2 3 4 5 →