Hydrosilylation of nitrogen-containing organic compounds: Model studies

Abstract

1,1,3,3-tetramethyldisiloxane (M2H) was used as the hydrosilylating agent for nitrogen-containing alkene derivatives: N-allylaniline (Naa), N-allylcyclohexylamine (Nach), N-allylpiperidine (Nap), 4-vinylpyridine (4VP) and 2-vinylpyridine (2VP). Reactions were performed in the presence of Pt0 complex (Karstedt's catalyst), in toluene, at 60 °C, for 24 h. Their course was followed by gas chromatography and FTIR spectroscopy. Final hydrosilylation products were characterized by FTIR, 1H, 13C and 29Si NMR spectroscopies as well as by elemental analysis. Total conversion of Si-H groups present in M2H in its reactions with N-allyl compounds was established, the process with Naa being the fastest. M2H reacted to a significantly lower degree with 2VP, while the reaction with 4VP did not occur. Results can be explained in terms of possible interactions of nitrogen atoms in alkene derivatives with Pt centers in the catalyst. The investigations model functionalization of siloxanes with nitrogen-containing groups via hydrosilylation conducted in the presence of Pt catalysts on which conflicting results are presented in the literature.