Synthetic routes to N-heterocyclic carbene complexes: Pyridine-carbene tautomerizations

被引:51
作者
Kunz, Doris [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
1,2 H-shift; C-H activation; carbenes; pyridines; tautomerization;
D O I
10.1002/anie.200700192
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) 70 years ago the existence of the 2-carbene isomer of pyridine, which arises by pyridine-carbene tautomerization (see scheme), was postulated. Now it has been prepared from pyridine as a stable carbene complex by metal-induced C-H activation. This pyridine-carbene tautomerization is described and discussed along with other analogous carbene tautomerization reactions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3405 / 3408
页数:4
相关论文
共 26 条
[1]   Iridium(III)-induced isomerization of 2-substituted pyridines to N-heterocyclic carbenes [J].
Alvarez, Eleuterio ;
Conejero, Salvador ;
Paneque, Margarita ;
Petronilho, Ana ;
Poveda, Manuel L. ;
Serrano, Oracio ;
Carmona, Ernesto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13060-13061
[2]   The mechanism of decarboxylation Part II The production of cyanide-like ions from alpha-picolinic, quinaldinic, and isoquinaldinac acids [J].
Ashworth, MRF ;
Daffern, RP ;
Hammick, DL .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :809-812
[3]   CHEMICAL EFFECTS OF STERIC STRAINS - A CENTENARY LECTURE DELIVERED AT BURLINGTON-HOUSE ON JUNE 2ND, 1955 [J].
BROWN, HC .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (MAY) :1248-1268
[4]   ORGANOMETALLIC CHEMISTRY OF VINYLIDENE AND RELATED UNSATURATED CARBENES [J].
BRUCE, MI .
CHEMICAL REVIEWS, 1991, 91 (02) :197-257
[5]   Ring strain perturbation of the equilibria between hydroxycarbene complexes and metal acyl hydride complexes [J].
Casey, CP ;
Czerwinski, CJ ;
Fusie, KA ;
Hayashi, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :3971-3978
[6]   Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams:: Involvement of direct carbonylation at olefinic C-H bonds as a key step [J].
Chatani, N ;
Kamitani, A ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7014-7018
[7]   Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring [J].
Chatani, N ;
Fukuyama, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :493-494
[8]   Coordinated carbenes from electron-rich olefins on RuHCl(PPri3)2 [J].
Coalter, JN ;
Bollinger, JC ;
Huffman, JC ;
Werner-Zwanziger, U ;
Caulton, KG ;
Davidson, ER ;
Gérard, H ;
Clot, E ;
Eisenstein, O .
NEW JOURNAL OF CHEMISTRY, 2000, 24 (01) :9-26
[9]   Stereoselective alkylation of α,β-unsaturated imines via C-H bond activation [J].
Colby, DA ;
Bergman, RG ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5604-5605
[10]   PENTAAMMINEOSMIUM(II)-ETA-2-2,6-LUTIDINE - AN INTERMEDIATE FOR C-H ACTIVATION [J].
CORDONE, R ;
TAUBE, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8101-8102