Ligand-Free Cu-Catalyzed Suzuki Coupling of Alkynyl Bromides with Boronic Acids in Ethanol Under Microwave Irradiation

被引：22

作者：

Babu, Sheba Ann ^{[1
]}

Saranya, Salim ^{[1
]}

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

Anilkumar, Gopinathan ^{[1
,2
]}

机构：

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

[2] Mahatma Gandhi Univ, AMMRC, Priyadarsini Hills PO, Kottayam 686560, Kerala, India

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 03期

关键词：

alkynyl bromides; boronic acids; Cu-catalysis; C-C bond formation; internal alkynes; Suzuki coupling; ARYL HALIDES; TERMINAL ALKYNES; EFFICIENT SONOGASHIRA; PALLADIUM-FREE; CARBON BONDS; IODIDES; PERSPECTIVES; MIYAURA; ELECTROPHILES; COMPLEXES;

D O I：

10.1002/slct.201803144

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ligand-free microwave assisted synthesis of internal alkynes using copper-catalyzed Suzuki type coupling reaction of alkynyl bromides with boronic acid derivatives has been developed. This protocol uses cheap CuI, greener solvent ethanol and K3PO4 base under microwave irradiation. This strategy does not need any ligand or sealed tube conditions. This methodology provides an efficient way to synthesize 1,2-diarylacetylenes in good to excellent yields.

引用

页码：1019 / 1022

页数：4

共 81 条

[1] Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine:: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
Alami, M
Crousse, B
Ferri, F
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 114 - 123
[2] Efficient copper-catalyzed Sonogashira coupling reactions and simulation studies
Ali, Imran
Nighot, Dnyaneshwar
Lone, Mohammad Nadeem
Jain, Arvind
[J]. SYNTHETIC COMMUNICATIONS, 2017, 47 (12) : 1175 - 1184
[3] Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives
Anastasia, L
Negishi, E
[J]. ORGANIC LETTERS, 2001, 3 (20) : 3111 - 3113
[4] [Anonymous], 2004, METAL CATALYZED CROS
[5] A Novel Protocol for the Cu-Catalyzed Sonogashira Coupling Reaction between Aryl Halides and Terminal Alkynes using trans-1,2-Diaminocyclohexane Ligand
Asha, Sujatha
Thomas, Anns Maria
Ujwaldev, Sankuviruthiyil M.
Anilkumar, Gopinathan
[J]. CHEMISTRYSELECT, 2016, 1 (13): : 3938 - 3941
[6] Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions
Batey, RA
Shen, M
Lough, AJ
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1411 - 1414
[7] The nickel-catalyzed Sonogashira-Hagihara reaction
Beletskaya, IP
Latyshev, GV
Tsvetkov, AV
Lukashev, NV
[J]. TETRAHEDRON LETTERS, 2003, 44 (27) : 5011 - 5013
[8] Beller M., 2008, TRANSITION METALS OR, V2
[9] Beutler U, 1996, CHIMIA, V50, P154
[10] Bolm, 2008, TRANSITION METALS OR, V1

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