Trace metal impurities in catalysis

被引:168
作者
Thome, Isabelle [1 ]
Nijs, Anne [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
IRON/COPPER COCATALYZED ALKYNYLATION; CARBON NANOTUBES; N-ARYLATION; COUPLING REACTION; ARYL IODIDES; SONOGASHIRA REACTION; CROSS-COUPLINGS; O-ARYLATION; ZINC METAL; PPB LEVELS;
D O I
10.1039/c2cs15249e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Metal-catalysed transformations are a powerful tool in organic chemistry and the enormous progress, which has been made in the last few decades, was one more time honoured by the Nobel Prize in Chemistry in 2010. Many metal-containing compounds have been applied in carbon-carbon and carbon-heteroatom bond formations. However, not every component originally claimed as catalyst turned out to be the active ingredient in the end. Sometimes trace metal impurities were the actual catalytic species. In this tutorial review, we will highlight recent findings in transition metal-catalysed cross-coupling reactions and detail several reports from the past, which illustrate that "trace metal catalysis" is not a newly discovered phenomenon.
引用
收藏
页码:979 / 987
页数:9
相关论文
共 97 条
[1]   Microwave-promoted Suzuki coupling reactions with organotrifluoroborates in water using ultra-low catalyst loadings [J].
Arvela, RK ;
Leadbeater, NE ;
Mack, TL ;
Kormos, CM .
TETRAHEDRON LETTERS, 2006, 47 (02) :217-220
[2]   A reassessment of the transition-metal free Suzuki-type coupling methodology [J].
Arvela, RK ;
Leadbeater, NE ;
Sangi, MS ;
Williams, VA ;
Granados, P ;
Singer, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168
[3]   KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2] [J].
ASHBY, MT ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :589-594
[4]   Carbon nanotubes contain metal impurities which are responsible for the "electrocatalysis" seen at some nanotube-modified electrodes [J].
Banks, CE ;
Crossley, A ;
Salter, C ;
Wilkins, SJ ;
Compton, RG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2533-2537
[5]   Iron-catalysed Suzuki coupling? A cautionary tale [J].
Bedford, Robin B. ;
Nakamura, Masaharu ;
Gower, Nicholas J. ;
Haddow, Mairi F. ;
Hall, Mark A. ;
Huwe, Michael ;
Hashimoto, Tohru ;
Okopie, Rukeme A. .
TETRAHEDRON LETTERS, 2009, 50 (45) :6110-6111
[6]   Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction (Retraction of vol 351, pg 1732, 2009) [J].
Bezier, David ;
Darcel, Christophe .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :1081-1081
[7]   RETRACTED: Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction (Retracted article. See vol. 352, pg. 1081, 2010) [J].
Bezier, David ;
Darcel, Christophe .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1732-1736
[8]   Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].
Bistri, Olivia ;
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588
[9]   Iron-catalyzed intramolecular O-arylation:: Synthesis of 2-aryl benzoxazoles [J].
Bonnamour, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2008, 10 (13) :2665-2667
[10]   Iron and Copper Salts in the Synthesis of Benzo[b]furans [J].
Bonnamour, Julien ;
Piedrafita, Maria ;
Bolm, Carsten .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1577-1581