Sulfonate functional carbene precursors and their features

The water soluble ligands were important for chemistry. They have application the ionic liquid and organocatalysis due to the ionic nature. The sulfonates, carbonates, ammonium groups and polyethers are among the most commonly used water soluble groups. Nowadays, the application of the NHC ligands sulfonate functionalized that important sulfonate functionalized the water soluble ligand groups are very common. The sulfonate groups are quite well dissolve in water due to the high acidity. Therefore, for more than 70 years it has been used in surfactant and detergent. In recent years, the ligands bearing sulfonate group and its application are quite common. For this purpose, in thesis the functionalized sulfonate new carbene precursors were synthesized, characterized and investigated in situ transition metal based catalytic performance for the alkylation reaction of amines. The results of this study could be summarized in two main sections: 1) 1,3-dialkylimidazolidinium (1a,b and 2a-c), 1,3-dialkyl benzimidazolium (3a-ü and 4a-ö) salts were synthesized and their structure were elucidated by spectroscopic techniques. 2) a) The catalytic activities of Ru-NHC complexes formed in situ conditions with synthesized propyl sulfonate group containing benzimidazolium salts (3a-n) have been tested in N-alkylation reactions of aniline and 2-aminopyridine with alcohols. b) The catalytic activities of Ru-NHC complexes formed in situ conditions with synthesized butyl sulfonate group containing benzimidazolium salts (4a-m) have been tested in N-C(3) dialkylation reactions of piperidine, pyrrolidine and morpholine with alcohols. c) The catalytic activities of Ru-NHC complexes formed in situ conditions with synthesized propyl sulfonate group containing benzimidazolium (3m-v) and imidazolidinium salts (2a-c) have been tested in C(3)-alkylation reactions of N-methylpiperidine with aldehyde derivatives. KEYWORDS: N-Heterocyclic carbene, sulfonate functionalized carbene, aniline, 2-aminopyridine, pyrrolidine, piperidine, morpholine, N-methylpiperidine, N-alkylation, N-C(3)-dialkylation.