4-Amino-3-pentadecyl-3H-1,2,4-triazole-3-thiones and 3-pentadecyl-1,3,4-oxadiazole-2(3H)-thione for the preparation of dimeric palladium(II) complexes and their applications in Tsuji-Trost and Mizoroki-Heck reactions

Abstract

The synthesis of palladium complexes derived from 4-amino-3-pentadecyl-3H-1,2,4-triazole-3-thiones and 3-pentadecyl-1,3,4-oxadiazole-2(3H)-thiones are reported. They were obtained from palladium acetate and dipotassium tetrachloropalladate(II) and their composition was assigned by elemental analysis (solid state). The resulting metallic entities were also characterized in solution based in mass spectrometry experiments. Their application in organic synthesis as cross-coupling reaction catalysts is described. One example of both conventional Tsuji-Trost and Mizoroki-Heck reactions were efficiently carried out in very high chemical yield.

GRAPHICAL ABSTRACT

Keywords:

• Mizoroki-Heck
• palladium
• palmitic acid
• Tsuji-Trost

Supplementary information (SI)

Supplementary material includes the characterization data of known compounds 1 and 2 ¹H and ¹³CNMR spectra of compounds 6, 9, and complexes 3a-d and ESI of complexes 3a-d.

Additional information

Funding

Financial support was provided by the Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and ConsoliderIngenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P, and CTQ2014-51912-REDC), FEDER, the GeneralitatValenciana (PROMETEO 2009/039 and PROMETEOII/2014/017) and the University of Alicante. M.C. thanks USTO-MB for scientific leave.