Metallacyclic Pyridylidene Structures from Reactions of Terminal Pyridylidenes with Alkenes and Acetylene

被引:37
作者
Alvarez, Eleuterio [1 ,2 ,3 ]
Hernandez, Yohar A. [1 ,2 ,3 ]
Lopez-Serrano, Joaquin [1 ,2 ,3 ]
Maya, Celia [1 ,2 ,3 ]
Paneque, Margarita [1 ,2 ,3 ]
Petronilho, Ana [1 ,2 ,3 ]
Poveda, Manuel L. [1 ,2 ,3 ]
Salazar, Veronica [4 ]
Vattier, Florencia [1 ,2 ,3 ]
Carmona, Ernesto [1 ,2 ,3 ]
机构
[1] CSIC, Inst Invest Quim, Seville 41092, Spain
[2] CSIC, Dpt Q Inorgan, Seville 41092, Spain
[3] Univ Seville, Seville 41092, Spain
[4] UAEH, Ctr Invest Quim, Pachuca, Hidalgo, Mexico
关键词
C-N coupling; cycloaddition reactions; iridium; nitrogen heterocycles; N-HETEROCYCLIC CARBENES; ANTI-MARKOVNIKOV HYDRATION; C-H ACTIVATION; ELECTROCHEMICAL PROPERTIES; CRYSTAL-STRUCTURES; NHC LIGANDS; COMPLEXES; PYRIDINE; METAL; COORDINATION;
D O I
10.1002/anie.201000608
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equotion Present). Iridium pyridyl species are key intermediates in the title reactions. Thermal elimination of benzene from complexes 1 (R = Me, Ph) creates a vacant coordination site accessible to unsaturated hydrocarbons. Subsequent intramolecular nucleophilic attack by the pyridyl nitrogen atom to the alkene or vinylidene leads to iridacyclic pyridylidene structures (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3496 / 3499
页数:4
相关论文
共 75 条
[1]   Catalytically active palladium pyridylidene complexes:: pyridinium ionic liquids as N-heterocyclic carbene precursors [J].
Albrecht, M ;
Stoeckli-Evans, H .
CHEMICAL COMMUNICATIONS, 2005, (37) :4705-4707
[2]   Rearrangement of pyridine to its 2-carbene tautomer mediated by iridium [J].
Alvarez, Eleuterio ;
Conejero, Salvador ;
Lara, Patricia ;
Lopez, Jorge A. ;
Paneque, Margarita ;
Petronilho, Ana ;
Poveda, Manuel L. ;
del Rio, Diego ;
Serrano, Oracio ;
Carmona, Ernesto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14130-+
[3]   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
[4]   All Kinds of Reactivity: Recent Breakthroughs in Metal-Catalyzed Alkyne Chemistry [J].
Anaya de Parrodi, Cecilia ;
Walsh, Patrick J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (26) :4679-4682
[5]   REACTION OF AN EARLY-TRANSITION-METAL ETA-2-SILAACYL COMPLEX WITH PYRIDINE - DIASTEREOSELECTIVITY IN THE FORMATION OF A (2-PYRIDYL)SILYLMETHOXY LIGAND [J].
ARNOLD, J ;
WOO, HG ;
TILLEY, TD ;
RHEINGOLD, AL ;
GEIB, SJ .
ORGANOMETALLICS, 1988, 7 (09) :2045-2049
[6]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[7]   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
[8]   Understanding the formation of N-H tautomers from α-substituted pyridines:: Tautomerization of 2-ethylpyridine promoted by osmiurn [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Garces, Karin ;
Olivan, Montserrat ;
Onate, Enrique .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10998-+
[9]  
Bustelo E., 2005, HDB C H TRANSFORMATI, V1
[10]  
Cabeza J. A., 2009, ANGEW CHEM, V121, P563