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

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2014年 / 2卷 / 03期

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

页码：500 / 505

页数：6

共 80 条

[21] Removal of Soluble Palladium Complexes from Reaction Mixtures by Fixed-Bed Adsorption [J].

Girgis, Michael J. ;

Kuczynski, Laura E. ;

Berberena, Sonia M. ;

Boyd, Caitlin A. ;

Kubinski, Pamela L. ;

Scherholz, Megerle L. ;

Drinkwater, Donald E. ;

Shen, Xiaoxuan ;

Babiak, Stanislaw ;

Lefebvre, Brian G. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (06) :1209-1217

[22] Glucose induced in-situ reduction of chloroaurate ions entrapped in a fatty amine film:: formation of gold nanoparticle-lipid composites [J].

Gole, A ;

Kumar, A ;

Phadtare, S ;

Mandale, AB ;

Sastry, M .

PHYSCHEMCOMM, 2001, (19)

[23] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[24] Acetylation of N-heteroaryl bromides via PdCl2/(o-tolyl)3P catalyzed Heck reactions [J].

He, Tianxiong ;

Tao, Xiaochun ;

Wu, Xinyan ;

Cai, Lisheng ;

Pike, Victor W. .

SYNTHESIS-STUTTGART, 2008, (06) :887-890

[25] Greener Techniques for the Synthesis of Silver Nanoparticles Using Plant Extracts, Enzymes, Bacteria, Biodegradable Polymers, and Microwaves [J].

Hebbalalu, Deepika ;

Lalley, Jacob ;

Nadagouda, Mallikarjuna N. ;

Varma, Rajender S. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (07) :703-712

[26] Expanding GSK's solvent selection guide - embedding sustainability into solvent selection starting at medicinal chemistry [J].

Henderson, Richard K. ;

Jimenez-Gonzalez, Concepcion ;

Constable, David J. C. ;

Alston, Sarah R. ;

Inglis, Graham G. A. ;

Fisher, Gail ;

Sherwood, James ;

Binks, Steve P. ;

Curzons, Alan D. .

GREEN CHEMISTRY, 2011, 13 (04) :854-862

[27] Magnetic copper-iron nanoparticles as simple heterogeneous catalysts for the azide-alkyne click reaction in water [J].

Hudson, Reuben ;

Li, Chao-Jun ;

Moores, Audrey .

GREEN CHEMISTRY, 2012, 14 (03) :622-624

[28] Green synthesis of metal nanoparticles using plants [J].

Iravani, Siavash .

GREEN CHEMISTRY, 2011, 13 (10) :2638-2650

[29] Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners [J].

Jana, Ranjan ;

Pathak, Tejas P. ;

Sigman, Matthew S. .

CHEMICAL REVIEWS, 2011, 111 (03) :1417-1492

[30] Searching for green solvents [J].

Jessop, Philip G. .

GREEN CHEMISTRY, 2011, 13 (06) :1391-1398

← 1 2 3 4 5 6 7 8 →