Supported gold nanoparticles catalyzed cis-selective semihydrogenation of alkynes using ammonium formate as the reductant

被引:45
作者
Liang, Shengzong [1 ]
Hammond, Gerald B. [1 ]
Xu, Bo [2 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
基金
美国国家科学基金会;
关键词
PALLADIUM; HYDROGENATION; ACTIVATION; FLUORINE; DIFLUOROMETHYLATION; SEMIREDUCTION; ACETYLENE; MIXTURES; LACTONE; REAGENT;
D O I
10.1039/c6cc01318j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
TiO2 supported gold nanoparticles with low loading (0.5 mol%) are able to semihydrogenate non -fluorinated and gem-difluorinated alkynes to cis-alkenes with high selectivity, using cost-effective and easy-to-handle ammonium formate as the reductant. No over-reduction was observed. The good recyclability of Au/TiO2 allows for "green" semireduction of alkynes. A difluorinated pyran and ce,p-unsaturated 8-lactone were easily prepared from the obtained gem-difluoro alkene building blocks.
引用
收藏
页码:6013 / 6016
页数:4
相关论文
共 76 条
[1]   Hydrogenation of Azides over Copper Nanoparticle Surface Using Ammonium Formate in Water [J].
Ahammed, Sabir ;
Saha, Amit ;
Ranu, Brindaban C. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (17) :7235-7239
[2]   Selective synthesis of fluorinated furan derivatives via AgNO3-catalyzed activation of an electronically deficient triple bond [J].
Arimitsu, Satoru ;
Hammond, Gerald B. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8559-8561
[3]   Formation of polymer-grade ethylene by selective hydrogenation of acetylene over Au/CeO2 catalyst [J].
Azizi, Yassine ;
Petit, Corinne ;
Pitchon, Veronique .
JOURNAL OF CATALYSIS, 2008, 256 (02) :338-344
[4]   Semihydrogenation of alkynes in the presence of Ni(0) catalyst using ammonia-borane and sodium borohydride as hydrogen sources [J].
Barrios-Francisco, Rigoberto ;
Garcia, Juventino J. .
APPLIED CATALYSIS A-GENERAL, 2010, 385 (1-2) :108-113
[5]   A Dehydratase Domain in Ambruticin Biosynthesis Displays Additional Activity as a Pyran-Forming Cyclase [J].
Berkhan, Gesche ;
Hahn, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (51) :14240-14244
[6]   DIALLYL (LITHIODIFLUOROMETHYL)PHOSPHONATE - A NEW REAGENT FOR THE INTRODUCTION OF THE (DIFLUOROMETHYLENE)PHOSPHONATE FUNCTIONALITY [J].
BERKOWITZ, DB ;
SLOSS, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7047-7050
[7]   A linear synthesis of gemcitabine [J].
Brown, Kylie ;
Weymouth-Wilson, Alex ;
Linclau, Bruno .
CARBOHYDRATE RESEARCH, 2015, 406 :71-75
[8]   Fundamental role of the fostriecin unsaturated lactone and implications for selective protein phosphatase inhibition [J].
Buck, SB ;
Hardouin, C ;
Ichikawa, S ;
Soenen, DR ;
Gauss, CM ;
Hwang, I ;
Swingle, MR ;
Bonness, KM ;
Honkanen, RE ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :15694-15695
[9]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[10]   Copper-Catalyzed Selective Semihydrogenation of Terminal Alkynes with Hypophosphorous Acid [J].
Cao, Huanyang ;
Chen, Tieqiao ;
Zhou, Yongbo ;
Han, Daoqing ;
Yin, Shuang-Feng ;
Han, Li-Biao .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :765-769