Pt Catalyzed Hydrosilylation of Fluorinated Phenoxy-Imine Ligands with Hydrosilanes

GRAPHICAL ABSTRACT

Abstract

The hydrosilylation reactions of three fluorinated phenoxy-imine ligands, N-(3-allylsalicylidene)-2,6-difluoroaniline(1), N-(3-allylsalicylidene)-2,3,5,6-tetrafluoroaniline(2) and N-(3-allylsalicylidene)-2,3,4,5,6-pentafluoroaniline (3), with triethoxysilane (TES) and 1,1,1,3,5,5,5-heptamethyltrisiloxane (MDHM) catalyzed by Pt complex (Pt-PMVS) has been studied. Three silylated products bearing Si-OEt bonds were prepared, after optimizing reaction conditions, the product selectivity were in the range of 51%∼59%, and followed the order 1>2>3. The products and byproducts were isolated and characterized by FT-IR, ¹H NMR, ¹³C NMR, ²⁹Si NMR, HRMS, and elemental analysis. As a comparison, other three silylated phenoxy-imine ligands were obtained by hydrosilylation of ligands with MDHM. The product selectivity were around 93%∼96%, and the side reactions were substantially suppressed.

Keywords:

• Hydrosilylation reactions
• fluorinated phenoxy-imine ligands
• product selectivity