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:1
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
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
收藏
页数:11
相关论文
共 65 条
[1]   Synthesis of Symmetrical Biaryls by Copper-Catalysed Homocoupling of Aryltriazenes in Guanidinium Ionic Liquid [J].
Anchi, Athmanand ;
Kumar, P. Pavan ;
Kalkhambkar, Rajesh G. ;
Naik, Ravi S. ;
Adam, Abdel Majid A. ;
Refat, Moamen S. ;
Mohammed Alsuhaibani, Amnah .
CHEMISTRYSELECT, 2023, 8 (37)
[2]   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 [J].
Anchi, Athmanand ;
Kalkhambkar, Rajesh G. ;
Kumar, P. Pavan ;
Naik, Ravi S. ;
Refat, Moamen S. ;
Adam, Abdel Majid A. ;
Alsuhaibani, Amnah Mohammed ;
Bakare, Safyah B. .
CHEMISTRYSELECT, 2023, 8 (23)
[3]   Tropylium-BF4 as Organocatalyst for Microwave-assisted Beckmann rearrangement in [TMG][BF4]: One-pot conversion of Ketones to Amides [J].
Anchi, Athmanand ;
Kalkhambkar, Rajesh G. ;
Sutar, Suraj M. ;
Naik, Ravi S. ;
Refat, Moamen S. ;
Adam, Abdel Majid A. ;
Mohammed Alsuhaibani, Amnah .
CHEMISTRYSELECT, 2023, 8 (23)
[4]   Aryltriazenes as Coupling Partners in the Hiyama, Hiyama-Suzuki and Hiyama-Heck Cross-Coupling Reactions Using Conventional and Ionic Liquid Reagents and Solvents [J].
Anchi, Athmanand ;
Malunavar, Shruti S. S. ;
Naik, Ravi S. S. ;
Kalkhambkar, Rajesh G. G. ;
Laali, Kenneth K. K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (45)
[5]   Tropylium-BF4 as Organocatalyst for Efficient Synthesis of Nitriles from Aldoximes; Synthetic Scope and Mechanistic Insights [J].
Anchi, Athmanand ;
Sutar, Suraj M. ;
Kalkhambkar, Rajesh G. ;
Borosky, Gabriela L. ;
Laali, Kenneth K. .
CHEMISTRYSELECT, 2022, 7 (35)
[6]   Accessing Heterobiaryls through Transition-Metal-Free C-H Functionalization [J].
Banik, Ananya ;
Paira, Rupankar ;
Shaw, Bikash Kumar ;
Vijaykumar, Gonela ;
Mandal, Swadhin K. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06) :3236-3244
[7]   A Versatile Catalyst System for Suzuki-Miyaura Cross-Coupling Reactions of C(sp2)-Tosylates and Mesylates [J].
Bhayana, Brijesh ;
Fors, Brett P. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2009, 11 (17) :3954-3957
[8]   Nickel-glycerol: an efficient, recyclable catalysis system for Suzuki cross coupling reactions using aryl diazonium salts [J].
Bhojane, Jeevan Manohar ;
Sarode, Sachin Ashok ;
Nagarkar, Jayashree Milind .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (02) :1564-1570
[9]   Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions [J].
Cheng, Kai ;
Wang, Chen ;
Ding, Yiyuan ;
Song, Qingbao ;
Qi, Chenze ;
Zhang, Xian-Man .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) :9261-9268
[10]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710