Reduction of carbonyl compounds via hydrosilylation : I. Hydrosilylation of carbonyl compounds catalyzed by tris(triphenylphosphine)chlororhodium |
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Authors: | Iwao Ojima Mitsuru Nihonyanagi Tetsuo Kogure Miyoko Kumagai Shuji Horiuchi Kimiyo Nakatsugawa Yoichiro Nagai |
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Institution: | Sagami Chemical Research Center, Nishi-Ohnuma 4-4-1, Sagamihara, Kanagawa 229 Japan;Department of Chemistry, Gunma University, Kiryu, Gunma 376 Japan |
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Abstract: | The hydrosilylation of various carbonyl compounds such as simple aldehydes, simple ketones, α,β-unsaturated carbonyl compounds, α-diketones, acyl cyanides and ketones having an electron-withdrawing group on the α-carbon using tris(triphenylphosphine)chlororhodium as a catalyst is described. Solvolysis of these silyl ethers and silyl enol ethers afforded the corresponding reduced products. The hydrosilylation of α,β-unsaturated carbonyl compounds was found to proceed by 1,4-addition. An oxidative adduct of triethylsilane to the rhodium-(I) complex was obtained as a reaction intermediate. The structure of the adduct was discussed on the basis of its IR and far-IR spectra. |
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