Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C-C bond formation

被引:31
作者
Iranpoor, Nasser [1 ]
Firouzabadi, Habib [1 ]
Davan, Elham Etemadi [1 ]
Rostami, Abed [1 ]
Nematollahi, Arash [1 ]
机构
[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz, Iran
关键词
Triphenyltin chloride; Pd(0); Cu(OAc)(2); O-; N-; and S-nucleophile; Aryl halide; STILLE COUPLING REACTIONS; EFFICIENT CATALYSTS; PALLADIUM CATALYSTS; PD NANOPARTICLES; MIZOROKI-HECK; ARYL HALIDES; N-ARYLATION; SUZUKI; REAGENTS; COMPLEX;
D O I
10.1016/j.jorganchem.2013.04.053
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)(2) in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110 degrees C is discussed. (C) 2013 Published by Elsevier B. V.
引用
收藏
页码:123 / 130
页数:8
相关论文
共 38 条
[1]   Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions [J].
Albisson, DA ;
Bedford, RB ;
Lawrence, SE ;
Scully, PN .
CHEMICAL COMMUNICATIONS, 1998, (19) :2095-2096
[2]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[3]  
[Anonymous], 2010, TETRAHEDRON, V66, P5451
[4]   The chemistry of pentavalent organobismuth reagents .14. Recent advances in the copper-catalyzed phenylation of amines. [J].
Arnauld, T ;
Barton, DHR ;
Doris, E .
TETRAHEDRON, 1997, 53 (12) :4137-4144
[5]   Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].
Calò, V ;
Nacci, A ;
Monopoli, A ;
Montingelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :6040-6044
[6]   Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates [J].
Chan, DMT ;
Monaco, KL ;
Li, RH ;
Bonne, D ;
Clark, CG ;
Lam, PYS .
TETRAHEDRON LETTERS, 2003, 44 (19) :3863-3865
[7]   Ligand-free Stille cross-coupling reaction using Pd/CaCO3 as catalyst reservoir [J].
Coelho, Aline V. ;
de Souza, Andrea Luzia F. ;
de Lima, Paulo G. ;
Wardell, James L. ;
Antunes, O. A. C. .
TETRAHEDRON LETTERS, 2007, 48 (43) :7671-7674
[8]   Stille coupling reactions catalysed by a polymer supported palladium complex [J].
Dell'Anna, MM ;
Lofù, A ;
Mastrorilli, P ;
Mucciante, V ;
Nobile, CF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (1-2) :131-137
[9]  
Dennis B.P., 2009, ACS NANO, V3, P1288
[10]   Ultrasound-assisted synthesis of unsymmetrical biaryls by Stille cross-coupling reactions [J].
Domini, Claudia E. ;
Silbestri, Gustavo F. ;
Band, Beatriz Fernandez ;
Chopa, Alicia B. .
ULTRASONICS SONOCHEMISTRY, 2012, 19 (03) :410-414