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Hydrosilylation of unsaturated compounds with 5-dimethylsilylfurfural diethyl acetal

Abstract

Hydrosilylation of terminal acetylenes, HC≡CR (R = CMe3,n-C7H15, SiMe3, Ph, COOEt, CH2N(CH2)4, and CH2N(CH2)5) with 5-dimethylsilylfurfural diethyl acetal (1) gives a mixture of products of bothtrans-β- and α-addition. When R = CMe3 or SiMe3, the reaction proceeds regio- and stereospecifically to give only thetrans-β-derivatives. The formation of β-adducts is favored by pronounced electron-donating substituents and steric hindrance at the Cα atom. Terminal alkenes, H2C=CHR (R = CH2CN, CH2N(CH2)4, CH2N(CH2)5, SiMe3, SiMe(α-furyl)2, SiMe2(α-furyl), SiMe2(α-thienyl), and SiMe2(5-chloro-2-thienyl)), react with silane1 to give only the products of β-addition; the reaction of1 with H2C=CHCH2NHC6H13-n affords a mixture of β- and α-adducts in a ratio of 1.8∶1.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1784–1788, October, 1993.

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Lukevics, E., Demicheva, L.E., Yerchak, N.P. et al. Hydrosilylation of unsaturated compounds with 5-dimethylsilylfurfural diethyl acetal. Russ Chem Bull 42, 1709–1712 (1993). https://doi.org/10.1007/BF00697047

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Key words

  • hydrosilylation
  • 5-dimethylsilylfurfural diethyl acetal
  • terminal acetylenes and alkenes
  • regioselectivity