Cyclometalated platinum(II) complexes bearing eugenol as effective catalyst for hydrosilylation of phenylacetylene by triethoxysilane

Pham Van Thong; Dinh Ngoc Doan Trang; Truong Thuy Hang; Nguyen Thi Thanh Chi

doi:10.15625/2525-2518/18442

Author affiliations

Authors

Pham Van Thong Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Ha Noi, Viet Nam
Dinh Ngoc Doan Trang Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Ha Noi, Viet Nam
Truong Thuy Hang Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Ha Noi, Viet Nam
Nguyen Thi Thanh Chi Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Ha Noi, Viet Nam https://orcid.org/0000-0002-0843-7237

DOI:

https://doi.org/10.15625/2525-2518/18442

Keywords:

Platinum complexes, eugenol, hydrosilylation, hydrogen and halogen bonds, 1H NMR spectra.

Abstract

The catalytic activities of the platinacyclic complexes bearing eugenol (EugH) including [Pt(μ-Cl)(Eug)]₂ (1) and [PtCl(Eug)(amine)] (2–4) [amine: pyridine/2, 4-methylpyridine/3, quinoline/4] for hydrosilylation of phenylacetylene by triethoxysilane have been studied for the first time. The results showed that the complexes 1–4 exhibited good catalytic abilities. With loading 0.5 mol% each of the catalysts 1–4 at 70 ^oC without solvents and any other additives in the air for 2 hours, the triethoxysilane was completely converted to (E)-triethoxy(styryl)silane) (β(E) – the major product) and (triethoxy(1-phenylvinyl)silane) (α – the minor product) with the α/β(E) molar ratio ranging from 1 : 2.6 to 1 : 2.8. At the same reaction conditions with loading 0.1 mol% each of the catalysts 2–4, the conversion of triethoxysilane slightly reduced with an efficiency of 97–99% and the α/β(E) molar ratio of 1 : 2.6 indicating the important role of the Pt-(C=C_alkene) in 1–4 for their catalytic activity. Furthermore, the verification of structures of complexes 2–4 by ¹³C NMR spectroscopy indicated that in chloroform-d₁, complex 3 formed two distinct structural forms due to strong intermolecular interactions between the chloroform solvent and the complex, including a Cl₃C-H...ClPt(II) hydrogen bond and a Cl₂HC-Cl...Pt(II) halogen bond.

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