Silver Complex of an N-Heterocyclic Carbene Ligand with Bulky Thiocarbamate Groups

• Autor(a) principal: Robles-Marín,Elvis
• Data de Publicação: 2018
• Outros Autores: Mondragón,Alexander, Flores-Alamo,Marcos, Castillo,Ivan
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000801751
• topic: carbenes; organic reactions; inorganic synthesis; spectroscopy

The synthesis of a new N-heterocyclic carbene with bulky S-arylthiocarbamate substituents was devised from the condensation between 2-chloromethyl-4-methy-l,6-[3,5-bis(trifluoromethyl)-phenyl]-S-phenyl-N,N-dimethylthiocarbamate and imidazole, resulting in the proligand N,N’-bis[(2-S-(N’’,N’’-dimethylthiocarbamoyl)-5-methyl)phenylmethyl]imidazolium iodide [H(S-carb)2NHC]I. This newly synthesized proligand was crystallographically characterized, thus confirming its identity; its stability was established in several solvents, resulting in air oxidation in methanolic solution, giving rise to the decomposition product N,N’-bis[(2-S-(N’’,N’’-dimethyl ­thiocarbamoyl)-5-methyl)phenylmethyl]-4,5-dimethoxyimidazolyl-2-one. Reaction of the proligand with silver oxide afforded the corresponding complex [(S-carb)2NHC]AgI, which was fully characterized by spectroscopic techniques.