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
  • [1] 1,3-Bis(N,N-dialkylamino)imidazolin-2-ylidenes: Synthesis and reactivity of a new family of stable N-heterocyclic carbenes
    Alcarazo, Manuel
    Roseblade, Stephen J.
    Alonso, Emma
    Fernandez, Rosario
    Alvarez, Eleuterio
    Lahoz, Fernando J.
    Lassaletta, Jose M.
    Journal of the American Chemical Society, 2004, 126 (41): : 13242 - 13243
  • [2] Conformational analysis of N,N′-dinaphthyl heterocyclic carbenes: imidazol-2-ylidenes and imidazolin-2-ylidenes
    Ibon Alkorta
    José Elguero
    Structural Chemistry, 2011, 22
  • [3] Conformational analysis of N,N′-dinaphthyl heterocyclic carbenes: imidazol-2-ylidenes and imidazolin-2-ylidenes
    Alkorta, Ibon
    Elguero, Jose
    STRUCTURAL CHEMISTRY, 2011, 22 (05) : 1087 - 1094
  • [4] Stable N-Heterocyclic Carbenes: N-Alkyl-N'-phosphanylbenzimidazol-2-ylidenes
    Marchenko, Anatoliy P.
    Koidan, Heorgiy N.
    Hurieva, Anastasiia N.
    Pervak, Igor I.
    Shishkina, Svitlana V.
    Shishkin, Oleg V.
    Kostyuk, Aleksandr N.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (21) : 4018 - 4033
  • [5] New approaches to the synthesis of N-heterocyclic carbenes
    Schlicht, Genna
    Odago, Maurice
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [6] Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a New Family of Stable Annulated N-Heterocyclic Carbenes: Synthesis, Reactivity, and Their Application in Coordination Chemistry and Organocatalysis
    Ma, Yajun
    Wei, Siping
    Lan, Jingbo
    Wang, Jingzhi
    Xie, Rugang
    You, Jingsong
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21): : 8256 - 8264
  • [7] Betaine Adducts of N-Heterocyclic Carbenes: Synthesis, Properties, and Reactivity
    Delaude, Lionel
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) : 1681 - 1699
  • [8] Stable N-Heterocyclic Carbenes with the N,N′-Diarylquinazolin-4-one Backbone: Improved Synthesis, Electronic Properties, and Reactivity
    Puetz, J. Maurice
    Hauer, Simone T.
    Nellesen, Joscha
    Deissenbeck, Daniel
    Mueller, Thomas J. J.
    Meisner, Jan
    Ganter, Christian
    ORGANOMETALLICS, 2024, 43 (02) : 141 - 163
  • [9] Synthesis of bis N-heterocyclic carbenes, derivatives and metal complexes
    Huffer, Arlanda
    Jeffery, Ben
    Waller, Benjamin J.
    Danopoulos, Andreas A.
    COMPTES RENDUS CHIMIE, 2013, 16 (06) : 557 - 565
  • [10] Phosphinoborenium cations stabilized by N-heterocyclic carbenes: synthesis, structure, and reactivity
    Kaniewska-Laskowska, Kinga
    Ordyszewska, Anna
    Wojnowski, Tomasz
    Halenka, Hanna
    Czapla, Marcin
    Chojnacki, Jaroslaw
    Grubba, Rafal
    DALTON TRANSACTIONS, 2023, 52 (43) : 16061 - 16066
12345