1,3-bis(N,N-dialkylamino)imidazolin-2-ylidenes:: Synthesis and reactivity of a new family of stable N-heterocyclic carbenes

被引：62
|
作者：
Alcarazo, M
Roseblade, SJ
Alonso, E
Fernández, R
Alvarez, E
Lahoz, FJ
Lassaletta, JM
机构：
[1] US, CSIC, Inst Invest Quim, E-41092 Seville, Spain
[2] Univ Seville, Dept Quim Organ, E-41012 Seville, Spain
[3] CSIC, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 41期
关键词：
D O I：
10.1021/ja0471119
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of stable 1,3-bis(N,N-dialkylamino)imidazolin-2-ylidenes was accomplished from readily available chiral bis-hydrazones after reduction or addition of PhMgCl, cyclization to imidazolinium salts, and treatment with KN(SiMe3)2. This strategy allows the obtention of free imidazolin-2-ylidenes and their Rh(COD)Cl complexes in enantiomerically pure form. The σ-donor ability of dialkylamino-substituted diaminocarbenes was found to be slightly higher than that of alkyl(aryl) analogues. Copyright © 2004 American Chemical Society.
引用
收藏
页码：13242 / 13243
页数：2
相关论文
共 50 条
  • [31] Exploring reactivity of the N-heterocyclic carbene, 1,3-bis(1-adamantyl)-imidazol-2-ylidene with group 13 metal halides
    DiSantis, Vincenzo M.
    Vohs, Jason K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [32] A New Class of Stable, Saturated N-Heterocyclic Carbenes with N-Naphthyl Substituents: Synthesis, Dynamic Behavior, and Catalytic Potential
    Vieille-Petit, Ludovic
    Luan, Xinjun
    Mariz, Ronaldo
    Blumentritt, Sascha
    Linden, Anthony
    Dorta, Reto
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) : 1861 - 1870
  • [33] Expanding the Chemistry of Cationic N-Heterocyclic Carbenes: Alternative Synthesis, Reactivity, and Coordination Chemistry
    Hildebrandt, Bjoern
    Raub, Stephan
    Frank, Walter
    Ganter, Christian
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (21) : 6670 - 6678
  • [34] Homologues of N-heterocyclic carbenes: Detection and electronic structure of N-bridgehead pyrido[a]-anellated 1,3,2-diazagermol-2-ylidenes
    Ullah, Farman
    Oprea, Anca I.
    Kindermann, Markus K.
    Bajor, Gabor
    Veszpremi, Tamas
    Heinicke, Joachim
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (03) : 397 - 403
  • [35] Free-radical polymerization of 2-[(N,N-dialkylamino)methyl]-1,3-butadienes.
    Sheares, VV
    Wu, LF
    Mohanty, AK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U367 - U367
  • [36] Stereoelectronic Characterization and Catalytic Potential of a 1,3-Bis(2,6-terphenyl)-Substituted N-Heterocyclic Carbene
    Twycross, Daniel
    Davey, Christopher J.
    Cole, Marcus L.
    McKay, Alasdair, I
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2021, 2021 (22) : 2133 - 2140
  • [37] Silver complexes of 1,2,4-triazole derived N-heterocyclic carbenes: Synthesis, structure and reactivity studies
    Dash, Chandrakanta
    Shaikh, Mobin M.
    Ghosh, Prasenjit
    JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (02) : 97 - 106
  • [38] Silver complexes of 1,2,4-triazole derived N-heterocyclic carbenes: Synthesis, structure and reactivity studies
    CHANDRAKANTA DASH
    MOBIN M SHAIKH
    PRASENJIT GHOSH
    Journal of Chemical Sciences, 2011, 123 : 97 - 106
  • [39] Synthesis of New Dipyrido-Annulated N-Heterocyclic Carbenes with Aryl Substituents
    Maeta, Naoto
    Yamamoto, Junki
    Fuku-en, Shin-ichi
    Shang, Rong
    Yamamoto, Yohsuke
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2015, 641 (12-13): : 2199 - 2203
  • [40] Synthesis and complexation of new multitopic non-chelating N-heterocyclic carbenes
    Tapu, Daniela
    Carter, Ashley
    Justice, Richard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
12345