Switching the Electron-Donor Properties of N-Heterocyclic Carbenes by a Facile Deprotonation Strategy

被引:89
作者
Biju, Akkattu T. [1 ]
Hirano, Keiichi [1 ]
Froehlich, Roland [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
carbenes; electronic properties; enolates; heterocycles; ligand design; RESTRICTED FLEXIBILITY; LIGANDS; COMPLEXES; CATALYSTS;
D O I
10.1002/asia.200900410
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Flip the switch! The facile and distinct variation of the electronic properties of an N-heterocyclic carbene (NHC) ligand is reported. In this process, a simple deprotonation/protonation strategy can render the NHC to be an electron-poor or an electron-rich NHC ligand: one ligand, two electronic natures. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1786 / 1789
页数:4
相关论文
共 47 条
[1]   The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides [J].
Altenhoff, G ;
Würtz, S ;
Glorius, F .
TETRAHEDRON LETTERS, 2006, 47 (17) :2925-2928
[2]   Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201
[3]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[4]  
Altenhoff G., 2003, Angew. Chem, V115, P3818, DOI [10.1002/ange.200351325, DOI 10.1002/ANGE.200351325]
[5]  
[Anonymous], ANGEW CHEM
[6]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[7]   Imidazol-2-ylidene-4-olate: an anionic N-heterocyclic carbene pre-programmed for further derivatization [J].
Benhamou, Laure ;
Cesar, Vincent ;
Gornitzka, Heinz ;
Lugan, Noel ;
Lavigne, Guy .
CHEMICAL COMMUNICATIONS, 2009, (31) :4720-4722
[8]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[9]   Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].
César, V ;
Bellemin-Laponnaz, S ;
Gade, LH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636
[10]   A stable anionic N-heterocyclic carbene and its zwitterionic complexes [J].
Cesar, Vincent ;
Lugan, Noel ;
Lavigne, Guy .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11286-+