One-Pot Palladium-Catalyzed Borrowing Hydrogen Synthesis of Thioethers

被引：39
作者：
Corma, Avelino [1 ]
Navas, Javier [1 ]
Rodenas, Tania [1 ]
Sabater, Maria J. [1 ]
机构：
[1] Inst Tecnol Quim UPV CSIC, Valencia 46022, Spain
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 51期
关键词：
heterogeneous catalysis; hydrogen transfer; palladium; synthetic methods; thioethers; EFFICIENT SYNTHESIS; GOLD; OXIDATION; SULFUR; THIOLS; SULFIDES; ALDEHYDES; DERIVATIVES; SELECTIVITY; ANTAGONISTS;
D O I：
10.1002/chem.201302226
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Palladium on magnesium oxide is able to allow a one-pot reaction to synthesize thioethers from thiols and aldehydes formed in situ from the respective alcohol by means of a borrowing hydrogen method. The reaction is initiated by dehydrogenation of the alcohol to give a palladium hydride intermediate and an aldehyde. The latter reacts with a thiol involving most probably the intermediacy of a thionium ion RCHS+R, which can be reduced in situ by the metal hydride to afford thioethers.
引用
收藏
页码：17464 / 17471
页数：8
相关论文
共 70 条
[1]   Efficient chemoselective alcohol oxidation using oxygen as oxidant.: Superior performance of gold over palladium catalysts [J].
Abad, Alberto ;
Almela, Carles ;
Corma, Avelino ;
Garcia, Hermenegildo .
TETRAHEDRON, 2006, 62 (28) :6666-6672
[2]  
[Anonymous], 2007, Angew. Chem.
[3]   Silica nanoparticles as a reusable catalyst: a straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts under neutral reaction conditions [J].
Banerjee, Subhash ;
Das, Jayanta ;
Alvarez, Richard P. ;
Santra, Swadeshmukul .
NEW JOURNAL OF CHEMISTRY, 2010, 34 (02) :302-306
[4]   DIFFUSION-CONTROLLED AND CONCERTED BASE CATALYSIS IN DECOMPOSITION OF HEMITHIOACETALS [J].
BARNETT, RE ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (24) :6758-&
[5]   Mechanism of selective alcohol oxidation to aldehydes on gold catalysts: Influence of surface roughness on reactivity [J].
Boronat, Mercedes ;
Corma, Avelino ;
Illas, Francesc ;
Radilla, Juan ;
Rodenas, Tania ;
Sabater, Maria J. .
JOURNAL OF CATALYSIS, 2011, 278 (01) :50-58
[6]   The active site in nanopaticle gold catalysis [J].
Campbell, CT .
SCIENCE, 2004, 306 (5694) :234-235
[7]   Muscarinic M2 antagonists: anthranilamide derivatives with exceptional selectivity and in vivo activity [J].
Clader, JW ;
Billard, W ;
Binch, H ;
Chen, LY ;
Crosby, G ;
Duffy, RA ;
Ford, J ;
Kozlowski, JA ;
Lachowicz, JE ;
Li, SJ ;
Liu, C ;
McCombie, SW ;
Vice, S ;
Zhou, GW ;
Greenlee, WJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (02) :319-326
[8]   MgO nanoparticle-based multifunctional catalysts in the cascade reaction allows the green synthesis of anti-inflammatory agents [J].
Climent, Maria Jose ;
Corma, Avelino ;
Iborra, Sara ;
Mifsud, Maria .
JOURNAL OF CATALYSIS, 2007, 247 (02) :223-230
[9]   Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures [J].
Climent, MJ ;
Corma, A ;
Iborra, S ;
Epping, K ;
Velty, A .
JOURNAL OF CATALYSIS, 2004, 225 (02) :316-326
[10]   Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].
Corma, A. ;
Leyva-Perez, A. ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712
1234567