Carbene Complexes Made Easily: Decomposition of Reissert Compounds and Further Synthetic Approaches

被引:28
作者
Bittermann, Agnes [1 ]
Baskakov, Denys [1 ]
Herrmann, Wolfgang A. [1 ]
机构
[1] Tech Univ Munich, Dept Chem, Chair Inorgan Chem, D-85747 Garching, Germany
关键词
N-HETEROCYCLIC CARBENES; TRANSITION-METAL-COMPLEXES; GROUP-TRANSFER POLYMERIZATION; CROSS-COUPLING REACTIONS; IRIDIUM COMPLEXES; PALLADIUM; LIGANDS; NHC; PRECURSORS; REACTIVITY;
D O I
10.1021/om900354v
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New methods for the preparation of NHC-metal complexes have been developed. It was shown that a nitrile group in Reissert analogous compounds can act as a good leaving group in thermal elimination, resulting in carbene formation. Moreover potassium carbonate was introduced as a highly efficient and mild reagent for the generation of N-heterocyclic carbene complexes in good to excellent yields, even in water, as the most environmentally friendly medium.
引用
收藏
页码:5107 / 5111
页数:5
相关论文
共 64 条
[1]  
Alder RW, 2002, CARBENE CHEMISTRY, P153
[2]   Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes [J].
Alder, RW ;
Blake, ME ;
Bufali, S ;
Butts, CP ;
Orpen, AG ;
Schütz, J ;
Williams, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1586-1593
[3]   Diaminocarbenes;: Calculation of barriers to rotation about Ccarbene-N bonds, barriers to dimerization, proton affinities, and 13C NMR shifts [J].
Alder, RW ;
Blake, ME ;
Oliva, JM .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (50) :11200-11211
[4]   Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].
Amyes, TL ;
Diver, ST ;
Richard, JP ;
Rivas, FM ;
Toth, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374
[5]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[6]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[7]   N-heterocyclic carbenes. 49. Chiral N-heterocyclic carbenes with restricted flexibility in asymmetric catalysis [J].
Baskakov, Denys ;
Herrmann, Wolfgang A. ;
Herdtweck, Eberhardt ;
Hoffmann, Stephan D. .
ORGANOMETALLICS, 2007, 26 (03) :626-632
[8]   Acceptor substituted N-heterocyclic carbenes and their Rh(I) complexes:: Synthesis, structure and properties [J].
Bittermann, Agnes ;
Haerter, Peter ;
Herdtweck, Eberhardt ;
Hoffmann, Stephan D. ;
Herrmann, Wolfgang A. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (12) :2079-2090
[9]   Quinoidal tetrazines:: Formation of a fascinating compound class [J].
Bostai, Beatrix ;
Novak, Zoltan ;
Benyei, Attila C. ;
Kotschy, Andras .
ORGANIC LETTERS, 2007, 9 (17) :3437-3439
[10]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91