Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki-Miyaura reaction

被引:57
作者
Das, Pankaj [1 ]
Bora, Utpal [1 ]
Tairai, Archana [1 ]
Sharma, Chandan [1 ]
机构
[1] Dibrugarh Univ, Dept Chem, Dibrugarh 786004, Assam, India
关键词
Suzuki-Miyaura reaction; Palladium chloride; Triphenylphosphine chalcogenides; CROSS-COUPLING REACTIONS; HIGHLY-ACTIVE CATALYST; ARYL CHLORIDES; PHOSPHINE OXIDES; COMPLEXES; PALLADIUM(0); PD/C; AMINATION; HALIDES; SYSTEM;
D O I
10.1016/j.tetlet.2010.01.032
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
A simple catalytic system based on PdCl2 and triphenylphosphine chalcogenides (PPh3X; X = O, S, Se) is found to be highly effective (up to 97% isolated yield) in the room temperature Suzuki-Miyaura reactions. Under the same experimental conditions, triphenylphosphine chalcogenides as ligands show superior activities compared to free triphenylphosphine. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1479 / 1482
页数:4
相关论文
共 46 条
[1]
Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds [J].
Ackermann, L ;
Born, R ;
Spatz, JH ;
Althammer, A ;
Gschrei, CJ .
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :209-214
[2]
Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex [J].
Bei, XH ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6797-6803
[3]
N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction [J].
Böhm, VPW ;
Gstöttmayr, CWK ;
Weskamp, T ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190
[4]
BRAUN L, 2007, J CHEM SOC DA, P1409
[5]
A family of simple amide-derived air-stable P,O-ligands for Suzuki cross-coupling of unactivated aryl chlorides [J].
Dai, WM ;
Zhang, Y .
TETRAHEDRON LETTERS, 2005, 46 (08) :1377-1381
[6]
Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates [J].
Denmark, Scott E. ;
Smith, Russell C. ;
Tymonko, Steven A. .
TETRAHEDRON, 2007, 63 (26) :5730-5738
[7]
Synthesis and characterisation of benzyl phosphino-thioether and -thiolato Pd(II) complexes and their applications in Suzuki coupling reactions [J].
Dervisi, Athanasia ;
Koursarou, Despina ;
Ooi, Li-ling ;
Horton, Peter N. ;
Hursthouse, Michael B. .
DALTON TRANSACTIONS, 2006, (48) :5717-5724
[8]
Determination of the stability constants for cobalt, nickel and palladium homogeneous catalyst complexes containing triphenylphosphine ligands [J].
Djekic, T. ;
Zivkovic, Z. ;
van der Ham, A. G. J. ;
de Haan, A. B. .
APPLIED CATALYSIS A-GENERAL, 2006, 312 :144-152
[9]
Pd/C: An old catalyst for new applications - Its use for the Suzuki-Miyaura reaction [J].
Felpin, Francois-Xavier ;
Ayad, Tahar ;
Mitra, Soumya .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (12) :2679-2690
[10]
A Triarylphosphine Ligand Bearing Dodeca(ethylene glycol) Chains: Enhanced Efficiency in the Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction [J].
Fujihara, Tetsuaki ;
Yoshida, Shohei ;
Terao, Jun ;
Tsuji, Yasushi .
ORGANIC LETTERS, 2009, 11 (10) :2121-2124