Glucose-Derived Palladium(0) Nanoparticles as in Situ-Formed Catalysts for Suzuki-Miyaura Cross-Coupling Reactions in Isopropanol

被引:46
作者
Camp, Jason E. [1 ]
Dunsford, Jay J. [1 ]
Cannons, Edward P. [1 ]
Restorick, William J. [1 ]
Gadzhieva, Anastasia [1 ]
Fay, Michael W. [2 ]
Smith, Robert J. [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Univ Nottingham, Nottingham Nanotechnol & Nanosci Ctr, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
Renewable sugars; Metal nanoparticles; Palladium catalysis; Alcoholic solvent; Energy-filtered transmission electron microscopy; N-HETEROCYCLIC CARBENES; ALPHA-D-GLUCOSE; GREEN SYNTHESIS; METAL NANOPARTICLES; MIZOROKI-HECK; GOLD NANOPARTICLES; NOBLE-METAL; PD; WATER; SONOGASHIRA;
D O I
10.1021/sc400410v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Effective and convenient protocols using renewable sugar-derived palladium(0) nanoparticles (PdNPs) as in situ-formed catalysts for Suzuki-Miyaura cross-coupling reactions in isopropanol under thermal and microwave heating conditions have been developed. The addition of a small amount of glucose (S mol %) to the reaction mixture lead to an increase in yield of the cross-coupled products compared to control experiments that omitted glucose. The size and morphology of the in situ-formed PdNPs were determined by TEM, and further EF-TEM analysis showed a hydrophilic hydroxylated shell around the individual palladium particles. The polar/hydrophilic nature of the nanoparticles allowed for their facile removal from the cross-coupled product, and a significant decrease in the amount of palladium incorporated into the final product was observed, as measured by ICP-MS analysis.
引用
收藏
页码:500 / 505
页数:6
相关论文
共 80 条
[1]   Biogenic Synthesis of Metallic Nanoparticles by Plant Extracts [J].
Akhtar, Mohd Sayeed ;
Panwar, Jitendra ;
Yun, Yeoung-Sang .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (06) :591-602
[2]   Suzuki-Miyaura cross-coupling reactions using a low-leaching and highly recyclable gold-supported palladium material and two types of microwave equipments [J].
Al-Amin, Mohammad ;
Akimoto, Masayoshi ;
Tameno, Tsuyoshi ;
Ohki, Yuuta ;
Takahashi, Naoyuki ;
Hoshiya, Naoyuki ;
Shuto, Satoshi ;
Arisawa, Mitsuhiro .
GREEN CHEMISTRY, 2013, 15 (05) :1142-1145
[3]   Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].
Astruc, Didier .
INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894
[4]   Rapid microwave-promoted Suzuki cross coupling reaction in water [J].
Bai, L ;
Wang, JX ;
Zhang, YM .
GREEN CHEMISTRY, 2003, 5 (05) :615-617
[5]   Removal of Heavy Metals from Organic Reaction Mixtures: Preparation and Application of Functionalized Resins [J].
Barbaras, Damien ;
Brozio, Jorg ;
Johannsen, Ib ;
Allmendinger, Thomas .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (06) :1068-1079
[6]   New functionalised silicas for highly selective cation exchange SPE purification in medicinal chemistry [J].
Brown, Jane ;
Chighine, Alessandra ;
Colucci, Marie A. ;
Galaffu, Nicola ;
Hirst, Simon C. ;
Seymour, Helen M. ;
Shiers, Jason J. ;
Wilkes, Robin D. ;
Williams, Jonathan G. ;
Wilson, John R. H. .
TETRAHEDRON LETTERS, 2008, 49 (33) :4968-4971
[7]   What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].
Capello, Christian ;
Fischer, Ulrich ;
Hungerbuehler, Konrad .
GREEN CHEMISTRY, 2007, 9 (09) :927-934
[8]   Biosynthesis of gold nanowires using sugar beet pulp [J].
Castro, Laura ;
Luisa Blazquez, M. ;
Munoz, Jesus A. ;
Gonzalez, Felisa ;
Garcia-Balboa, Camino ;
Ballester, Antonio .
PROCESS BIOCHEMISTRY, 2011, 46 (05) :1076-1082
[9]   Monoligated palladium species as catalysts in cross-coupling reactions [J].
Christmann, U ;
Vilar, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374
[10]   Heterogeneous Sonogashira Coupling over Nanostructured SiliaCat Pd(0) [J].
Ciriminna, Rosaria ;
Pandarus, Valerica ;
Gingras, Genevieve ;
Beland, Francois ;
Cara, Piera Demma ;
Pagliaro, Mario .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (01) :57-61