N-heterocyclic carbenes. IV.1synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety

2011 ◽  
Vol 23 (1) ◽  
pp. 5-15 ◽  
Author(s):  
V. A. Glushkov ◽  
K. A. Arapov ◽  
M. S. Kotelev ◽  
K. S. Rudowsky ◽  
K. Yu. Suponitsky ◽  
...  
Keyword(s):  
Heterocyclic Carbenes ◽  
Imidazolium Salts

scholarly journals Scalable Synthesis of 1,3,4,5-Tetraaryl Imidazolium Salts as Precursors of Sterically Demanding N-Heterocyclic Carbenes

SynOpen ◽  
2020 ◽  
Vol 04 (01) ◽  
pp. 01-11
Author(s):  
Cengiz Azap ◽  
Anna Christoffers ◽  
Renat Kadyrov
Keyword(s):  
Large Scale ◽  
Oxidative Desulfurization ◽  
Heterocyclic Carbenes ◽  
Imidazolium Salts ◽  
Imidazolium Salt ◽  
Available N ◽  
Sterically Demanding ◽  
Cost Efficient ◽  
Scalable Synthesis ◽  
Electron Donation

A convenient, large-scale, and cost-efficient synthesis of 4,5-diarylsubstituted N,N-diarylimidazolium salts is described. A variety of 1,3,4,5-tetraaryl imidazolium salts with increasing electron donation and steric bulk of the N-aryl groups was synthesized in good yields. In the key step, readily available N,N′-diarylthioureas and benzoin/anisoin are coupled to give imidazole-2-thiones, followed by imidazolium salt formation by oxidative desulfurization. In this way, N,N-diarylimidazolium salts with 2-methoxy, 2-methyl, and 2-isopropyl substituents could be obtained; the synthesis of their 2-tert-butyl, 2,6-dimethyl, and 2,6-diisopropyl analogues failed.

Selective Activation of Fluoroalkenes with N-Heterocyclic Carbenes: Synthesis of N-Heterocyclic Fluoroalkenes and Polyfluoroalkenyl Imidazolium Salts

2016 ◽  
Vol 22 (24) ◽  
pp. 8063-8067 ◽  
Author(s):  
Matthew C. Leclerc ◽  
Serge I. Gorelsky ◽  
Bulat M. Gabidullin ◽  
Ilia Korobkov ◽  
R. Tom Baker
Keyword(s):  
Heterocyclic Carbenes ◽  
Imidazolium Salts ◽  
Selective Activation

Thiazole-Annelated Imidazolium Salts: A New Architecture for N-Heterocyclic Carbenes

Synthesis ◽  
2008 ◽  
Vol 2008 (14) ◽  
pp. 2221-2228 ◽  
Author(s):  
Frank Glorius ◽  
Claudia Lohre ◽  
Roland Fröhlich
Keyword(s):  
Heterocyclic Carbenes ◽  
Imidazolium Salts

scholarly journals Synthesis and Characterization of Ag(I) Complexes Derived from New N-Heterocyclic Carbenes

2019 ◽  
Vol 31 (5) ◽  
pp. 1149-1152
Author(s):  
Mohammed Mujbel Hasson ◽  
Basim H. Al-Zaidi ◽  
Ahmad H. Ismail
Keyword(s):  
Spectral Analysis ◽  
Heterocyclic Carbenes ◽  
Synthesis And Characterization ◽  
Silver Complexes ◽  
Imidazolium Salts ◽  
Imidazole Derivatives ◽  
In Situ Method ◽  
Transitional Metal

Two new unsymmetrical imidazolium salts viz., [1-(4-ethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (3) and [1-(2,6-dimethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (4) have been synthesized via the reaction of propyl bromide with imidazole derivatives, [1-(4-ethylphenyl)-1Himidazole] (1) and [1-(2,6-dimethylphenyl)-1H-imidazole] (2) in absence of solvent. Then two new N-heterocyclic carbene silver complexes (5 and 6) were prepared through the reaction of imidazoluim salts (3 and 4) as a source of N-heterocyclic carbene with Ag2O by in situ method. These complexes can be used in the future as a transfer agent for preparing other transitional metal carbine complexes (NHCs) via transmetallation method. The formation of these compounds was confirmed by spectral analysis.

N-Heterocyclic Carbenes: V. Synthesis of imidazolium salts from lupane series

2012 ◽  
Vol 48 (5) ◽  
pp. 699-704 ◽  
Author(s):  
V. A. Glushkov ◽  
M. A. Zhiguleva ◽  
O. A. Maiorova ◽  
A. A. Gorbunov
Keyword(s):  
Heterocyclic Carbenes ◽  
Imidazolium Salts

Nickel-catalysed direct C2-arylation of N-heterocyclic carbenes

2017 ◽  
Vol 46 (36) ◽  
pp. 12027-12031 ◽  
Author(s):  
Nga Kim T. Ho ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
Vitor H. Menezes da Silva ◽  
Daniel G. Watanabe ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Reductive Elimination ◽  
Heterocyclic Carbenes ◽  
Imidazolium Salts

Direct C2-arylation of NHCs to C2-arylated imidazolium salts (III) is achieved using Ni-catalysis. The dinuclear Ni(i) species I undergoes oxidative addition with ArX to give the Ni(ii) intermediate II. Reductive elimination delivers the arylation product III and regenerates the catalyst I.

scholarly journals Cationic 5-phosphonio-substituted N-heterocyclic carbenes

2016 ◽  
Vol 45 (28) ◽  
pp. 11384-11396 ◽  
Author(s):  
Kai Schwedtmann ◽  
Robin Schoemaker ◽  
Felix Hennersdorf ◽  
Antonio Bauzá ◽  
Antonio Frontera ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Heterocyclic Carbenes ◽  
Imidazolium Salts ◽  
Dehydrogenation Reactions

Cationic NHCs featuring a phosphonium moiety in the 5-position are prepared from the reaction of imidazolium salts with a tert. phosphane. They are used as ligands for the preparation of transition metal complexes, dehydrogenation reactions of prim. and sec. phosphanes and the preparation of a N-heterocyclic olefin (NHO).

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