Reaction of p-(trimethylsilyl)benzaldehyde with organomagnesium compounds

Furan derivatives of group IV elements (review)

“…The yield of the products from the hydrosilylation of furfural by hydrosilanes R3SiH in the presence of chloroplatinic acid is low, and even after heating at 120°C for 78 h more than 50% of the initial reagents remain unreacted. The reaction with 2-acetylfuran takes place with even greater difficulty, and in this case only traces of the product were detected [2141, If nickel chloride or a mixture of nickel chloride with diethyl sulfide is used as catalyst, mixtures of mono-and disilyl products are formed in ratios of 34%:29% and 23~{ 57% respectively [216]~ Similar results were obtained in [217] It was possible to increase the yield substantially and to avoid the side processes by conducting hydrosilylation under mild conditions at room temperature in methylene chloride in the presence of catalytic amounts of cesium chloride and the phase-transfer agent 18-crown-6 ether [215]. The yield of the products from hydrosilylation of furfural and 2-acetylfurfural by dimethylphenylsilane under these conditions amounts to 67 and 61% respectively.…”

“…The furfuryloxy derivatives of silicon and tin can be synthesized from f\lrfuryl alcohol in reactions with silicon disulfide [212] Various catalysts have been used in this reaction: Chloroplatinic acid [214], nickel chloride [216], colloidal nickel [217], various rhodium metal-complex catalysts [218], a 1:2 mixture of dibutyldiacetylacetonatostannane and dibutyldi(cyclohexyloxy)stanmme [224], and cesium and rubidium chlorides in the presence of 18-crown-6 [215,221]. The yield of the products from the hydrosilylation of furfural by hydrosilanes R3SiH in the presence of chloroplatinic acid is low, and even after heating at 120°C for 78 h more than 50% of the initial reagents remain unreacted.…”