Synthesis of thiol esters promoted by copper oxide nanoparticle, in the presence of ionic liquid under microwave irradiation

Synthesis of thiol esters promoted by copper oxide nanoparticle, in the presence of ionic liquid under microwave irradiation

Azeredo, Juliano B.; Godoi, Marcelo; Galetto, Fábio Z.; Botteselle, Giancarlo Viccari; Nascimento, Vanessa; Braga, Antonio L.

Abstract:

Thiol esters are versatile building blocks used for organic transformations. It can be used in C-C coupling, for the synthesis of various organic compounds and application in native chemical ligation for peptide bond formation, in natural product synthesis. They are biologically active substance and investigated in vivo tumor suppression and as anti-HIV agents. On the other hand, nanotechnology has become an attractive emerging field for catalysis. Nanoscale heterogeneous catalysts offer higher surface area and low-coordinated sites, which are responsible for the higher catalytic activity. In the present work, we have developed a new synthetic methodology for the synthesis of thiol esters, starting from acid chloride, diorganoyl disulfides and copper oxide nanoparticle as catalyst. In addition, we used ionic liquid as the solvent under microwave irradiation conditions. The work result in an environmentally friendly methodology for the synthesis of structurally diverse thiol esters, in which the use of bases or reducing agents were omitted.

Thiol esters are versatile building blocks used for organic transformations. It can be used in C-C coupling, for the synthesis of various organic compounds and application in native chemical ligation for peptide bond formation, in natural product synthesis. They are biologically active substance and investigated in vivo tumor suppression and as anti-HIV agents. On the other hand, nanotechnology has become an attractive emerging field for catalysis. Nanoscale heterogeneous catalysts offer higher surface area and low-coordinated sites, which are responsible for the higher catalytic activity. In the present work, we have developed a new synthetic methodology for the synthesis of thiol esters, starting from acid chloride, diorganoyl disulfides and copper oxide nanoparticle as catalyst. In addition, we used ionic liquid as the solvent under microwave irradiation conditions. The work result in an environmentally friendly methodology for the synthesis of structurally diverse thiol esters, in which the use of bases or reducing agents were omitted.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0089-1

Referências bibliográficas

• [1] 1 Turpin, J. A.; Song, Y.; Inman, J. K.; Huang, M.; Wallqvist, A.; Maynard, A.; Covell, D. G.; Rice, W. G.; Appella, E. J. Med. Chem. 1999, 42, 67-86.
• [2] 2 Singh, D.; Narayanaperumal, S.; Gul, K.; Godoi, M.;Rodrigues, O. E. D.;Braga, A. L.Green Chem.2010, 12, 957 – 960.

Como citar:

Azeredo, Juliano B.; Godoi, Marcelo; Galetto, Fábio Z.; Botteselle, Giancarlo Viccari; Nascimento, Vanessa; Braga, Antonio L.; "Synthesis of thiol esters promoted by copper oxide nanoparticle, in the presence of ionic liquid under microwave irradiation", p-89-89. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0089-1