Mono-and dinuclear cyclopalladates as catalysts for Suzuki-Miyaura cross-coupling reactions in predominantly aqueous media

被引:16
作者
Babu, G. Narendra [1 ]
Pal, Samudranil [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
Cyclopalladates; Mono-and dinuclear; Suzuki-Miyaura cross-coupling; Aqueous media; FREE SONOGASHIRA REACTIONS; ROOM-TEMPERATURE; ARYL CHLORIDES; NEAT WATER; PALLADIUM NANOPARTICLES; EFFICIENT CATALYST; AEROBIC CONDITIONS; ARYLBORONIC ACIDS; LIGANDS SYNTHESES; COMPLEXES;
D O I
10.1016/j.tetlet.2017.01.089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Suzuki-Miyaura cross-coupling reactions of aryl halides with arylboronic acids were performed in predominantly aqueous media employing two mono-and two dinuclear cyclopalladated complexes as catalysts. These complexes are [Pd(HL)Cl] (I), [Pd(L)(PPh3)] (II), [Pd-2(y-dppb)(L)(2)] (III) and [Pd-2(mu-dppf)(L)2] (IV); where H2L, dppb and dppf represent 4-methoxy-N'-(mesitylidene)benzohydrazide, 1,4-bis (diphenylphosphino)butane and 1,1'-bis(diphenylphosphino)ferrocene, respectively. The reactions were conducted using potassium carbonate as base in presence of tetrabutylammonium bromide (TBAB) at 70/90 degrees C in dimethylformamide-water (1:20) mixture. Among the four catalysts used, the dinuclear complex IV turned out to be the most effective and afforded moderate to excellent yields with broad substrate scope. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1000 / 1005
页数:6
相关论文
共 55 条
[41]   Triphenylphosphinopalladium(II) complexes with ONO-donor ligands: syntheses, structures and catalytic applications in CC cross-coupling reactions [J].
Prabhu, Rupesh Narayana ;
Babu, G. Narendra ;
Pal, Samudranil .
APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (01)
[42]   Copper-free Sonogashira reactions catalyzed by a palladium(II) complex bearing pyrenealdehyde thiosemicarbazonate under ambient conditions [J].
Prabhu, Rupesh Narayana ;
Pal, Samudranil .
TETRAHEDRON LETTERS, 2015, 56 (37) :5252-5256
[43]   Enantioselective Fluorescent Sensors: A Tale of BINOL [J].
Pu, Lin .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (02) :150-163
[44]   Palladacycle containing nitrogen and selenium: highly active pre-catalyst for the Suzuki-Miyaura coupling reaction and unprecedented conversion into nano-sized Pd17Se15 [J].
Rao, Gyandshwar Kumar ;
Kumar, Arun ;
Ahmed, Jahangeer ;
Singh, Ajai Kumar .
CHEMICAL COMMUNICATIONS, 2010, 46 (32) :5954-5956
[45]   Synthesis of biaryls via a nickel(0)-catalyzed cross-coupling reaction of chloroarenes with arylboronic acids [J].
Saito, S ;
Ohtani, S ;
Miyaura, N .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8024-8030
[46]   LIQUID-CRYSTALS AND CHIRALITY - APPLICATION TO THE DETERMINATION OF ABSOLUTE-CONFIGURATIONS AND TO THE CONFORMATIONAL-ANALYSIS OF BIARYLS [J].
SOLLADIE, G ;
GOTTARELLI, G .
TETRAHEDRON, 1987, 43 (07) :1425-1437
[47]   Benzaldimines as ligands for palladium in Suzuki-Miyaura reactions [J].
Srimani, Dipankar ;
Sarkar, Amitabha .
TETRAHEDRON LETTERS, 2008, 49 (44) :6304-6307
[48]   Bio-Waste Corn-cob Cellulose Supported Poly(amidoxime) Palladium Nanoparticles for Suzuki-Miyaura Cross-Coupling Reactions [J].
Sultana, T. ;
Mandal, Bablu Hira ;
Rahman, Md. Lutfor ;
Sarkar, Shaheen M. .
CHEMISTRYSELECT, 2016, 1 (13) :4108-4112
[49]   Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct C-C Bonds (Nobel Lecture) [J].
Suzuki, Akira .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) :6722-6737
[50]   Efficient synthesis of 3-aryl-1H-indazol-5-amine by Pd-catalyzed Suzuki-Miyaura cross-coupling reaction under microwave-assisted conditions [J].
Wang, Shengqiang ;
Guo, Ruiyun ;
Li, Jingya ;
Zou, Dapeng ;
Wu, Yangjie ;
Wu, Yusheng .
TETRAHEDRON LETTERS, 2015, 56 (24) :3750-3753