Pd/C-Catalyzed Homocoupling Reaction for the Synthesis of Symmetrical Biaryl Diamides

被引:5
作者
Shen, Guodong [1 ]
Wang, Yichen [1 ]
Zhao, Xiliang [1 ]
Huangfu, Xinlei [1 ]
Tian, Yanmeng [1 ]
Zhang, Tongxin [1 ]
Yang, Bingchuan [1 ]
机构
[1] Liaocheng Univ, Sch Pharm, Sch Chem & Chem Engn, Liaocheng 252000, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
Pd/C; homocoupling reaction; symmetrical biaryl diamides; 2-halo-N-phenylbenzamides; recyclability; CROSS-COUPLING REACTIONS; ARYL BOND FORMATION; HETEROGENEOUS PALLADIUM; HECK CHEMISTRY; CARBON; SUZUKI; HYDROGENATION; COMPLEXES;
D O I
10.1055/s-0036-1588437
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd/C was found to be an efficient and convenient metal catalyst in the homocoupling reaction for the synthesis of symmetrical biaryl diamides. The catalyst system Pd/C-KOAc showed high catalytic activity, and a variety of symmetrical biaryl diamides were conveniently synthesized from 2-halo-N-phenylbenzamides in moderate to good yields.
引用
收藏
页码:2030 / 2035
页数:6
相关论文
共 38 条
[1]   Low temperature recyclable catalyst for Heck reactions using ultrasound [J].
Ambulgekar, GV ;
Bhanage, BM ;
Samant, SD .
TETRAHEDRON LETTERS, 2005, 46 (14) :2483-2485
[2]   Amidate ligand design effects in zirconium-catalyzed enantioselective hydroamination of aminoalkenes [J].
Ayinla, Rashidat O. ;
Gibson, Travis ;
Schafer, Laurel L. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) :50-60
[3]  
Biswas A.K., 1992, CHEM BER, V125, P2325
[4]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[5]   Palladium-Catalyzed, tert-Butyllithium-Mediated Dimerization of Aryl Halides and Its Application in the Atropselective Total Synthesis of Mastigophorene A [J].
Buter, Jeffrey ;
Heijnen, Dorus ;
Vila, Carlos ;
Hornillos, Valentin ;
Otten, Edwin ;
Giannerini, Massimo ;
Minnaard, Adriaan J. ;
Feringa, Ben L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) :3620-3624
[6]   Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides [J].
Chen, Yi-An ;
Liu, Ching-Yuan .
RSC ADVANCES, 2015, 5 (91) :74180-74188
[7]   Suzuki-Miyaura cross-coupling with quasi-heterogeneous palladium [J].
Conlon, DA ;
Pipik, B ;
Ferdinand, S ;
LeBlond, CR ;
Sowa, JR ;
Izzo, B ;
Collins, P ;
Ho, GJ ;
Williams, JM ;
Shi, YJ ;
Sun, YK .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :931-935
[8]   Pd-zeolites as heterogeneous catalysts in Heck chemistry [J].
Dams, M ;
Drijkoningen, L ;
Pauwels, B ;
Van Tendeloo, G ;
De Vos, DE ;
Jacobs, PA .
JOURNAL OF CATALYSIS, 2002, 209 (01) :225-236
[9]   Mechanism of a Suzuki-Type Homocoupling Reaction Catalyzed by Palladium Nanocubes [J].
Elias, Welman C. ;
Signori, Aline M. ;
Zaramello, Laize ;
Albuquerque, Brunno L. ;
de Oliveira, Daniela C. ;
Domingos, Josiel B. .
ACS CATALYSIS, 2017, 7 (02) :1462-1469
[10]   ULLMANN SYNTHESIS OF BIARYLS [J].
FANTA, PE .
SYNTHESIS-STUTTGART, 1974, (01) :9-21