Efficient synthesis of vinyl and alkyl sulfides via hydrothiolation of alkynes and electron-deficient olefins using soluble and heterogenized gold complexes catalysts

被引:99
作者
Corma, Avelino [2 ]
Gonzalez-Arellano, Camino [1 ,3 ]
Iglesias, Marta [1 ]
Sanchez, Felix [3 ]
机构
[1] CSIC, Inst Ciencia Mat Madrid, Madrid 28049, Spain
[2] Univ Politecn Valencia, Inst Tecnol Quim, CSIC, Valencia 46022, Spain
[3] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
Hydrothiolation; Alkyl sulfides; Vinyl sulfides; Heterogenized catalysts; Gold catalysts; ANTI-MARKOVNIKOV HYDROAMINATION; MICHAEL ADDITION; METAL-COMPLEXES; BOND FORMATION; C-S; THIOLS; PALLADIUM; ALKENES; VINYLARENES; GOLD(III);
D O I
10.1016/j.apcata.2009.12.016
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Soluble and heterogenized gold complexes catalyze the hydrothiolation of alkynes and electron-deficient olefins in high yields and with high anti-Markovnikov selectivity. Moreover heterogenized catalysts could be recycled in several successive runs without any loss of activity or selectivity. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:49 / 54
页数:6
相关论文
共 39 条
[1]   Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes [J].
Ananikov, VP ;
Malyshev, DA ;
Beletskaya, IP ;
Aleksandrov, GG ;
Eremenko, IL .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) :1993-2001
[2]   Mesoporous MCM41-heterogenised (salen)Mn and Cu complexes as effective catalysts for oxidation of sulfides to sulfoxides -: Isolation of a stable supported Mn(V)=O complex, responsible of the catalytic activity [J].
Ayala, V ;
Corma, A ;
Iglesias, M ;
Sánchez, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 221 (1-2) :201-208
[3]  
BACKVALL JE, 1994, J ORG CHEM, V59, P5850
[4]   Native silica nanoparticle catalyzed anti-Markovnikov addition of thiols to inactivated alkenes and alkynes: a new route to linear and vinyl thioethers [J].
Banerjee, Subhash ;
Das, Jayanta ;
Santra, Swadeshmukul .
TETRAHEDRON LETTERS, 2009, 50 (01) :124-127
[5]   A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES [J].
BECK, JS ;
VARTULI, JC ;
ROTH, WJ ;
LEONOWICZ, ME ;
KRESGE, CT ;
SCHMITT, KD ;
CHU, CTW ;
OLSON, DH ;
SHEPPARD, EW ;
MCCULLEN, SB ;
HIGGINS, JB ;
SCHLENKER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10834-10843
[6]   Unusual influence of the structures of transition metal complexes on catalytic C-S and C-Se bond formation under homogeneous and heterogeneous conditions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3431-3444
[7]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[8]  
Beller M, 1999, CHEM-EUR J, V5, P1306, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1306::AID-CHEM1306>3.3.CO
[9]  
2-W
[10]   A USEFUL METHOD FOR CONFIGURATIONAL ASSIGNMENT OF VINYL SULFIDES - STEREOCHEMICAL REASSESSMENT OF THE RADICAL-ADDITION OF BENZENETHIOL TO ALKYNES [J].
BENATI, L ;
CAPELLA, L ;
MONTEVECCHI, PC ;
SPAGNOLO, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1035-1038