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Synlett 1995; 1995(12): 1232-1234
DOI: 10.1055/s-1995-5250
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Palladium-Catalyzed Hydrosilation of 1-Alkynes with Concomitant Dimerization to Form 1,3-Dienylsilanes

Yukio Kawanami, Keiji Yamamoto*
  • *Department of Chemical Engineering, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
31 December 2000 (online)

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Palladium(0) complexes obtained in-situ from 1/2 [(η3-C3H5)PdCl]2 + 2 P(OAr)3 catalyze the hydrosilation of 1-alkynes with HSiCl3 at room temperature to yield 1,3-dienylsilane derivatives in which alkyne dimerization accompanies hydrosilation. The head-to-tail adduct, R-CH=CH-C(R)=CHSiCl3 (2), predominates over the regioisomeric one, H2C=C(R)-C(R)=CHSiCl3 (3). The ratios 2/3 are proportional to the increase in cone angle of the phosphite ligands, tri-2,6-xylylphosphite being of the best choice in a ratio 11:1.

Hydrosilation - 1-Alkyne - Palladium catalyst - Dimerization