Abstract
In 2010, A. Suzuki was awarded the Nobel Prize in Chemistry together with R. Heck and E. Negishi for their study of C−C cross-coupling reactions [1] which are of great relevance in organic synthesis [2] and thus, in industrial processes and in pharmaceuticals. Palladium based compounds appear to be outstanding catalysts in the C−C cross-coupling reactions [3], and although there are commercially available catalysts such as [Pd(PPh3)4] or [Pd(OAc)2], they fail to comply with air and thermal stability, so by tuning the ligands this problem can be overcome. Given our vast experience in the synthesis and characterization of this type of compounds [4] with thiosemicarbazones as ligands, and their use as catalysts in the Suzuki-Miyaura reaction [5] within this communication we present the synthesis, characterisation and applicability of a family of palladium compounds to the Suzuki-Miyaura reaction. References [1] http://www.nobelprize.org/nobel_prizes/chemistry/laureates/2010/ [2] J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, New York, 1995 [3] I. P. Belestkaya, A. V. Cheprakov; J. Organomet. Chem. 2004, 689, 4055. [4] B. Bermúdez Puente Compuestos Ciclometalados de Paladio y Platino. Reacciones de acoplamiento y catálisis. PhD Dissertation. Santiago de Compostela 2014. [5] N. Miyaura, K Yamada, A. Suzuki Tetrahedron, 1979, 36, 3437.
Highlights
Carbon−Carbon cross−coupling reactions are of great relevance in organic synthesis [1] and in industrial and in pharmaceutical processes
Palladium based compounds appear to be outstanding catalysts in the C−C cross−coupling reactions [2], and there are commercially available catalysts such as [Pd(PPh3)4] or [Pd(OAc)2], they fail to comply with air and thermal stability, so by tuning the ligands this problem can be overcome
3.4 Catalysis: the catalysis proves were carried out in a Radley Carousel 12 Plus Reaction Station with 6mL of a mixture of solvents THF:water 1:2, using as substrates 4-bromoanisole, 4-bromoacetophenone and phenylboronic acid and K3PO4 as base. This communication shows that thiosemicarbazones act as bidentate ligands and their coordination towards the metal is in the thiol form as shown by 1H NMR, IR and X-ray diffraction
Summary
Carbon−Carbon cross−coupling reactions are of great relevance in organic synthesis [1] and in industrial and in pharmaceutical processes. Thiosemicarbazones are a family of ligands formed by the reaction between a carbonyl group and a tiosemicarbazide. They present different coordination modes from mono to tetradentate due to the presence of a variety of donor atoms in their structure, and in solution they present thiol–thione equilibrium [3]; their most common coordinative fashion is as bidentate ligands forming a five membered ring, which is the most stable [4]. Thiosemicarbazone ligands themselves are known for showing cytotoxic activity. For this reason the combination of both functions makes palladium – thiosemicarbazone compounds an interesting new tool in chemistry
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