Transition metal catalyzed Glaser and Glaser-Hay coupling reactions: Scope, classical/green methodologies and synthetic applications

被引:41
作者
Akhtar, Rabia [1 ]
Zahoor, Ameer Fawad [1 ]
机构
[1] Govt Coll Univ Faisalabad, Dept Chem, Faisalabad 38000, Pakistan
关键词
Glaser cross coupling; macrocyclization; nanoparticles; palladium; silver; PSEUDO 5-COMPONENT SYNTHESIS; TERMINAL ALKYNES; HOMOCOUPLING REACTION; BINAPHTHYL POLYMERS; EFFICIENT SYNTHESIS; SONOGASHIRA; OPTIMIZATION; LIGAND; 1,3-BUTADIYNES; RADIAANNULENES;
D O I
10.1080/00397911.2020.1802757
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Glaser coupling is one of the most important modern organic tool for the formation of carbon-carbon triple bond and has also been extensively used for the synthesis of polymers, macrocycles and oligomers (known for their electrochemical, optical and electronic properties). Although this reaction is generally catalyzed by copper complexes yet recent advances including new ligands, additives and silver/cobalt/palladium catalysts make this coupling reaction more effective. This review highlights the role of various catalytic systems used in Glaser- and Glaser-Hay coupling reactions for the production of a variety of C-C triple bonds with wide structural features.
引用
收藏
页码:3337 / 3368
页数:32
相关论文
共 92 条
[31]   Synthesis, properties, and FET performance of rectangular oligothiophene [J].
Ie, Yutaka ;
Hirose, Tomoya ;
Aso, Yoshio .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (43) :8169-8175
[32]   Flexibility of Shape-Persistent Molecular Building Blocks Composed of p-Phenylene and Ethynylene Units [J].
Jeschke, Gunnar ;
Sajid, Muhammad ;
Schulte, Miriam ;
Ramezanian, Navid ;
Volkov, Aleksei ;
Zimmermann, Herbert ;
Godt, Adelheid .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (29) :10107-10117
[33]   Cu(II)-promoted oxidative homocoupling reaction of terminal alkynes in supercritical carbon dioxide [J].
Jiang, HF ;
Tang, JY ;
Wang, AZ ;
Deng, GH ;
Yang, SR .
SYNTHESIS-STUTTGART, 2006, (07) :1155-1161
[34]   Conjugated microporous poly (aryleneethynylene) networks [J].
Jiang, Jia-Xing ;
Su, Fabing ;
Trewin, Abbie ;
Wood, Colin D. ;
Campbell, Nell L. ;
Niu, Hongjun ;
Dickinson, Calum ;
Ganin, Alexey Y. ;
Rosseinsky, Matthew J. ;
Khimyak, Yaroslav Z. ;
Cooper, Andrew I. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) :8574-8578
[35]   Toward a mechanistic understanding of oxidative homocoupling: the Glaser-Hay reaction [J].
Jover, Jesus ;
Spuhler, Philipp ;
Zhao, Ligang ;
McArdle, Ciaran ;
Maseras, Feliu .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (12) :4200-4209
[36]  
Kabalka GW, 2001, SYNLETT, P108
[37]   Transition-metal-free variant of Glaser- and Cadiot-Chodkiewicz-type Coupling: Benign access to diverse 1,3-diynes and related molecules [J].
Kaldhi, Dhananjaya ;
Vodnala, Nagaraju ;
Gujjarappa, Raghuram ;
Kabi, Arup K. ;
Nayak, Subhashree ;
Malakar, Chandi C. .
TETRAHEDRON LETTERS, 2020, 61 (16)
[38]   Tuning of cross-Glaser products mediated by substrate-catalyst polymeric backbone interactions [J].
Kaur, Sharanjeet ;
Mukhopadhyaya, Aritra ;
Selim, Abdul ;
Gowri, Vijayendran ;
Neethu, K. M. ;
Dar, Arif Hassan ;
Sartaliya, Shaifali ;
Ali, Md. Ehesan ;
Jayamurugan, Govindasamy .
CHEMICAL COMMUNICATIONS, 2020, 56 (17) :2582-2585
[39]   Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira-Glaser Cyclization Sequence [J].
Klukas, Fabian ;
Perkampus, Joerg ;
Urselmann, Dominik ;
Mueller, Thomas J. J. .
SYNTHESIS-STUTTGART, 2014, 46 (24) :3415-3422
[40]   Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence [J].
Klukas, Fabian ;
Grunwald, Alexander ;
Menschel, Franziska ;
Mueller, Thomas J. J. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :672-679