Isothiouronium salts as useful and odorless intermediates for the synthesis of thiaalkylimidazolium ionic liquids

TETRAHEDRON LETTERS

卷:60

Article

Matiello, Gabriela I.¹  Pazini, Alessandra^1,2  da Silva, Kacris I. M.¹  da Costa, Rafaela G. M.²  Ebeling, Gunter¹  Dupont, Jairton¹  Limberger, Jones²  Scholten, Jackson D.¹ 

[1] Univ Fed Rio Grande do Sul, Inst Chem, Lab Mol Catalysis, Ave Bento Goncalves 9500, BR-91501970 Porto Alegre, RS, Brazil

[2] Pontifical Catholic Univ Rio de Janeiro, Dept Chem, Rua Marques de Sao Vicente 225, BR-22451900 Rio De Janeiro, RJ, Brazil

关键词: Ionic liquids;    Sulfur compounds;    Isothiouronium salts;    Cross-coupling;   

DOI  :  10.1016/j.tetlet.2019.02.013

来源: Elsevier

【 摘 要 】

A simple and odorless route for the synthesis of monocationic and dicationic thiaalkylimidazolium ionic liquids (ILs) is reported. Our approach starts with the selective monoalkylation of dihalogenated substrates by methylimidazole derivatives, followed by the synthesis of odorless isothiouronium salts via reaction with thiourea. The target ILs are obtained after sequential hydrolysis-alkylation of the isothiouronium salts followed by anion metathesis in water. After extraction, the novel thiaalkylimidazolium ILs are obtained with high purity, without the requirement of additional purification steps. In order to demonstrate their applicability, two of these task-specific ILs were employed as ligands in Ullmann and Suzuki couplings and also as charged probes to detect copper intermediates via ESI(+)-MS. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free