Carboxylation of N-H/C-H Bonds Using N-Heterocyclic Carbene Copper(I) Complexes

被引：283

作者：

Boogaerts, Ine I. F. ^{[1
]}

Fortman, George C. ^{[1
]}

Furst, Marc R. L. ^{[1
]}

Cazin, Catherine S. J. ^{[1
]}

Nolan, Steven P. ^{[1
]}

机构：

[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 46期

基金：

英国工程与自然科学研究理事会;

关键词：

carbene ligands; carboxylation; C-H activation; copper catalysts; N heterocycles; CATALYZED OXIDATIVE CARBONYLATION; CARBON-DIOXIDE; ALKENYLBORONIC ESTERS; ORGANIC-SYNTHESIS; C-C; CO2; ACTIVATION; FUNCTIONALIZATION; 2-OXAZOLIDINONES; OXINDOLES;

D O I：

10.1002/anie.201004153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Greenhouse gas makes good: A simple copper-mediated protocol has been developed where N-H or C-H bonds can be directly functionalized using an easily prepared catalyst. The novel [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] copper(I) hydroxide, [Cu(IPr)(OH)], permits the facile activation and carboxylation of N-H and C-H bonds with pKavalues of less than 27.7 (see scheme). © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8674 / 8677

页数：4

共 39 条

[1] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[2]

Bercaw J.E., 2008, Angew. Chem, V120, P10089

[3] C-H Bond Activation by [{(Diimine)Pd(μ-OH)}2]2+ Dimers: Mechanism-Guided Catalytic Improvement [J].

Bercaw, John E. ;

Hazari, Nilay ;

Labinger, Jay A. ;

Oblad, Paul F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9941-9943

[4] Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes [J].

Boogaerts, Ine I. F. ;

Nolan, Steven P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8858-+

[5]

Brown D J., 2004, The Chemistry of Heterocyclic Compounds

[6] Simple and versatile synthesis of copper and silver N-heterocyclic carbene complexes in water or organic solvents [J].

Citadelle, Cecilia A. ;

Le Nouy, Erwan ;

Bisaro, Fabrice ;

Slawin, Alexandra M. Z. ;

Cazin, Catherine S. J. .

DALTON TRANSACTIONS, 2010, 39 (19) :4489-4491

[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[8] Activation of carbon-hydrogen bonds via 1,2-addition across M-X (X = OH or NH2) bonds of d6 transition metals as a potential key step in hydrocarbon functionalization:: A computational study [J].

Cundari, Thomas R. ;

Grimes, Thomas V. ;

Gunnoe, T. Brent .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :13172-13182

[9] N-Heterocyclic Carbenes in Late Transition Metal Catalysis [J].

Diez-Gonzalez, Silvia ;

Marion, Nicolas ;

Nolan, Steven P. .

CHEMICAL REVIEWS, 2009, 109 (08) :3612-3676

[10]

Flessner T, 1999, J PRAK CHEM-CHEM ZTG, V341, P186, DOI 10.1002/(SICI)1521-3897(199902)341:2<186::AID-PRAC186>3.0.CO

← 1 2 3 4 →