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

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 35期

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

页码：6013 / 6016

页数：4

共 76 条

[11] Synthesis of γ-Monofluorinated Goniothalamin Analogues via Regio- and Stereoselective Ring-Opening Hydrofluorination of Epoxide [J].

Chen, Jun-Ling ;

Zheng, Feng ;

Huang, Yangen ;

Qing, Feng-Ling .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6525-6533

[12] Ammonia recycling enables sustainable operation of bioelectrochemical systems [J].

Cheng, Ka Yu ;

Kaksonen, Anna H. ;

Cord-Ruwisch, Ralf .

BIORESOURCE TECHNOLOGY, 2013, 143 :25-31

[13] Chemicals from Alkynes with Palladium Catalysts [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826

[14] Selective Semihydrogenation of Alkynes on Shape-Controlled Palladium Nanocrystals [J].

Chung, Jooyoung ;

Kim, Chanhoi ;

Jeong, Hansaem ;

Yu, Taekyung ;

Binh, Do Huy ;

Jang, Jyongsik ;

Lee, Jaichan ;

Kim, B. Moon ;

Lim, Byungkwon .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (05) :919-925

[15] A Well-Defined Pd Hybrid Material for the Z-Selective Semihydrogenation of Alkynes Characterized at the Molecular Level by DNP SENS [J].

Conley, Matthew P. ;

Drost, Ruben M. ;

Baffert, Mathieu ;

Gajan, David ;

Elsevier, Cornelis ;

Franks, W. Trent ;

Oschkinat, Hartmut ;

Veyre, Laurent ;

Zagdoun, Alexandre ;

Rossini, Aaron ;

Lelli, Moreno ;

Lesage, Anne ;

Casano, Gilles ;

Ouari, Olivier ;

Tordo, Paul ;

Emsley, Lyndon ;

Coperet, Christophe ;

Thieuleux, Chloe .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (37) :12234-12238

[16] Supported gold nanoparticles as catalysts for organic reactions [J].

Corma, Avelino ;

Garcia, Hermenegildo .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (09) :2096-2126

[17] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].

Dorel, Ruth ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072

[18] Convenient Transfer Semihydrogenation Methodology for Alkynes Using a PdII-NHC Precatalyst [J].

Drost, Ruben M. ;

Bouwens, Tessel ;

van Leest, Nicolaas P. ;

de Bruin, Bas ;

Elsevier, Cornelis J. .

ACS CATALYSIS, 2014, 4 (05) :1349-1357

[19] Hydrogen Dissociation by Gold Clusters [J].

Fujitani, Tadahiro ;

Nakamura, Isao ;

Akita, Tomoki ;

Okumura, Mitsutaka ;

Haruta, Masatake .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9515-9518

[20] A New Reagent for Direct Difluoromethylation [J].

Fujiwara, Yuta ;

Dixon, Janice A. ;

Rodriguez, Rodrigo A. ;

Baxter, Ryan D. ;

Dixon, Darryl D. ;

Collins, Michael R. ;

Blackmond, Donna G. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1494-1497

← 1 2 3 4 5 6 7 8 →