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Hydrosilylation of Aromatic Aldehydes and Ketones Catalyzed by Mono- and Tri-Nuclear Platinum(0) Complexes

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Hydrosilylation of aromatic aldehydes and acetophenone with H2SiPh2 was studied by using Pt complexes as the catalyst. Reaction of aromatic aldehydes, such as PhCHO, 4-FC6H4CHO, 4-MeC6H4CHO and 4-CF3C6H4CHO with H2SiPh2… Click to show full abstract

Hydrosilylation of aromatic aldehydes and acetophenone with H2SiPh2 was studied by using Pt complexes as the catalyst. Reaction of aromatic aldehydes, such as PhCHO, 4-FC6H4CHO, 4-MeC6H4CHO and 4-CF3C6H4CHO with H2SiPh2 in the presence of [Pt(PPh3)3] catalyst proceeds smoothly at room temperature with similar reaction rates. The hydrosilylation of PhCHO with H2Si(C6H4-4-Me)2 proceeds faster than that with H2SiPh2. Comparison of the reactions of PhCHO with H2SiPh2 and with D2SiPh2 demonstrated a large kinetic isotope effect (3.1). The hydrosilylation of the aldehydes catalyzed by [Pt(PMe3)(μ-SiPh2)]3, reported in our previous paper, shows large dependence of the reaction rate on the aryl group of the substrate, in the order, 4-MeC6H4CHO ≫ PhCHO = 4-FC6H4CHO > 4-CF3C6H4CHO. Hydrosilylation of (3-vinyl)benzaldehyde and 10-undecenal in the presence of [Pt(PPh3)3] catalyst occurs at the carbonyl group selectively to form the corresponding alkoxysilanes. The hydrosilylation of acetophenone with H2SiPh2 catalyze...

Keywords: hydrosilylation aromatic; h2siph2; aldehydes ketones; ketones catalyzed; aromatic aldehydes; hydrosilylation

Journal Title: Bulletin of the Chemical Society of Japan
Year Published: 2018

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