Aryl/Hetero-Aryl Tosylates as Coupling Partners in Metal-Mediated Suzuki and Hiyama Cross-Coupling Reactions in Ionic Liquids: Ligand-Free Facile Synthesis of Biaryls/Heterobiaryls

被引：0

作者：

Jadhav, Vinod ^{[1
]}

Kurahatti, Sunita ^{[1
]}

Anchi, Athmanand ^{[1
]}

Jamadar, Imamhusen ^{[1
]}

Kalkhambkar, Rajesh G. ^{[1
]}

Sutar, Suraj M. ^{[2
]}

Kurkuri, Mahaveer ^{[3
]}

Refat, Moamen S. ^{[4
]}

Alsuhaibani, Amnah Mohammed ^{[5
]}

机构：

[1] Karnatak Univ, Dept Chem, Karnatak Sci Coll, Dharwad 580001, Karnataka, India

[2] Yashwantrao Chavan Mahavidyalaya, Dept Chem, Halkarni 416552, Maharashtra, India

[3] JAIN Deemed Univ, Ctr Res Funct Mat CRFM, Jain Global Campus, Bengaluru 562112, Karnataka, India

[4] Taif Univ, Coll Sci, Dept Chem, POB 11099, Taif 21944, Saudi Arabia

[5] Princess Nourah Bint Abdulrahman Univ, Coll Sport Sci & Phys Act, Dept Phys Sport Sci, Riyadh 11671, Saudi Arabia

来源：

CHEMISTRYSELECT | 2024年 / 9卷 / 41期

关键词：

Aryl/hetero-aryl tosylates; Biaryls; Catalysis; Cross-coupling reactions; Green chemistry; Ionic liquids; PALLADIUM CATALYST; IMIDAZOLIUM-ILS; EFFICIENT; MIYAURA; ARENESULFONATES; HALIDES; HECK; SYSTEM; SONOGASHIRA; LIBRARIES;

D O I：

10.1002/slct.202403925

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diverse libraries of biaryls/heterobiaryls were synthesized by aryl/hetero-aryl tosylates as coupling partners in the ligand-free, Ni-catalyzed Suzuki coupling reaction, and Pd-catalyzed Hiyama cross-coupling reaction in ionic liquids (ILs) as green solvent. In this method easily available and economically viable tosylates were coupled with readily available boronic acids and phenyltriethoxysilanes in Suzuki and Hiyama cross-coupling respectively to yield the corresponding biaryls/heterobiaryls. Mild reaction condition(s), easy workup, moderate to excellent yield of the isolated pure products, wide substrate scope, and recycling/reuse of the ILs are the advantages of this method over the other reported methods.

引用

页数：11

共 36 条

[1] Synthesis of Biaryls via Ligand-Free Suzuki-Miyaura Cross-Coupling Reactions: A Review of Homogeneous and Heterogeneous Catalytic Developments
Hussain, Ibrar
Capricho, Jaworski
Yawer, Mirza A.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (21) : 3320 - 3349
[2] Phosphane-Free Hiyama Cross-Coupling of Aryl and Heteroaryl Halides Catalyzed by Palladium Nanoparticles in Ionic Liquids
Premi, Chanchal
Jain, Nidhi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5493 - 5499
[3] Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions
Bandgar, BP
Bettigeri, SV
Phopase, J
TETRAHEDRON LETTERS, 2004, 45 (37) : 6959 - 6962
[4] Pd/C-Catalyzed Ligand-Free Hiyama Cross-Coupling Reaction of Aryl Halides Under Aqueous Conditions
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Mukkanti, Khagga
Reguri, Buchi Reddy
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[5] Recent advances in transition metal-catalysed cross-coupling of (hetero)aryl halides and analogues under ligand-free conditions
Ayogu, Jude I.
Onoabedje, Efeturi A.
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[6] The synthesis of 4′-aryl substituted terpyridines by Suzuki cross-coupling reactions:: substituent effects on ligand fluorescence
Goodall, W
Wild, K
Arm, KJ
Williams, JAG
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[7] Nickel-catalysed Suzuki-Miyaura cross-coupling reactions of aryl halides with arylboronic acids in ionic liquids
Wang, Man
Yuan, Xiaobin
Li, Hongyu
Ren, Limin
Sun, Zhizhong
Hou, Yanjun
Chu, Wenyi
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[8] A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross-coupling reactions using NFSac as CO source
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Kumar, P. Pavan
Naik, Ravi S.
Refat, Moamen S.
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[9] Mechanistic Facets of the Competition between Cross-Coupling and Homocoupling in Supporting Ligand-Free Iron-Mediated Aryl-Aryl Bond Formations
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Lefevre, Nicolas
Ahr, Mathieu
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[10] Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions
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