Palladium-bis(oxazoline) complexes with inherent chirality: Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions

被引:46
作者
Hussain, S. M. Shakil [2 ]
Ibrahim, Mansur B. [1 ]
Fazal, Atif [3 ]
Suleiman, Rami [4 ]
Fettouhi, Mohammed [1 ]
El Ali, Bassam [1 ]
机构
[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
[2] King Fahd Univ Petr & Minerals, Ctr Petr & Minerals, Dhahran 31261, Saudi Arabia
[3] King Fahd Univ Petr & Minerals, Ctr Res Excellence Petr Refining & Petrochem, Dhahran 31261, Saudi Arabia
[4] King Fahd Univ Petr & Minerals, Ctr Res Excellence Corros, Dhahran 31261, Saudi Arabia
关键词
Palladium; Bis(oxazoline); Inherent chirality; Coupling reactions; BIS(OXAZOLINE) LIGANDS; MIYAURA REACTION; PALLADIUM; CATALYST;
D O I
10.1016/j.poly.2013.12.023
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New palladium-bis(oxazoline) (Pd-BOX) complexes were synthesized and characterized. The X-ray crystal structures of the two complexes showed that the palladium ion is bound to the nitrogen atoms of the two heterocycles of the bidentate ligand and two chloride ions in a distorted square planar geometry. The coordination to the palladium ion allows these non C-2-symmetric bis(oxazoline) ligand-based complexes to acquire a rigid backbone curvature generating an inherent chirality. The catalytic activities were evaluated in Suzuki-Miyaura, Mizorold-Heck and Sonogashira coupling reactions. The complexes showed high catalytic activities towards numerous C-C coupling reactions with various aryl halides, aryl boronic acids, alkenes and alkynes. The reactions were optimized for the most suitable temperature, solvent, and base system. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:39 / 46
页数:8
相关论文
共 35 条
[1]   Synthesis of new chiral diimine palladium(II) and nickel(II) complexes bearing oxazoline- and myrtanyl-based nitrogen ligands.: Crystal structure of the C2-symmetric complex [{(1R,2S)-inda-box}PdCl2] [J].
Abu-Surrah, AS ;
Kettunen, M ;
Lappalainen, K ;
Piironen, U ;
Klinga, M ;
Leskelä, M .
POLYHEDRON, 2002, 21 (01) :27-31
[2]  
[Anonymous], SADABS PROGRAM FOR E
[3]   Suzuki, Heck, and copper-free Sonogashira reactions catalyzed by 4-amino-5-methyl-3-thio-1,2,4-triazole-functionalized polystyrene resin-supported Pd(II) under aerobic conditions in water [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Jajarmi, Saeideh .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 724 :206-212
[4]   Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki-Miyaura reactions in aqueous media [J].
Banik, Biplab ;
Tairai, Archana ;
Shahnaz, Nasifa ;
Das, Pankaj .
TETRAHEDRON LETTERS, 2012, 53 (42) :5627-5630
[5]  
Bruker, 2008, SMART AND SAINT
[6]  
Buchwald SL, 2008, ACCOUNTS CHEM RES, V41, P1439, DOI 10.1021/ar8001798
[7]   Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution [J].
Buden, Maria E. ;
Guastavino, Javier F. ;
Rossi, Roberto A. .
ORGANIC LETTERS, 2013, 15 (06) :1174-1177
[8]   Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water [J].
Cheng, Kai ;
Zhao, Baoli ;
Hu, Sai ;
Zhang, Xian-Man ;
Qi, Chenze .
TETRAHEDRON LETTERS, 2013, 54 (46) :6211-6214
[9]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[10]   DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].
COREY, EJ ;
IMAI, N ;
ZHANG, HY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729