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Stereospecific synthesis of a family of novel (E)-2-aryl-1-silylalka-1,4-dienes or (E)-4-aryl-5-silylpenta-1,2,4-trienes via a crosscoupling of (Z)-silyl(stannyl)ethenes with allyl halides or propargyl bromide is described. In the reaction with allyl bromide, either a Pd(dba) 2 -CuI combination (dba, dibenzylideneacetone) in DMF or copper(I) iodide in DMSO-THF readily catalyzes or mediates the coupling reaction of (Z)-silyl(stannyl)ethenes at room temperature, producing novel vinylsilanes bearing an allyl group β to silicon with cis-disposition in good yields. Allyl chlorides as halides can be used in the CuI-mediated reaction. CuI alone much more effectively mediates the cross-coupling reaction with propargyl bromide in DMSO-THF at room temperature compared with a Pd(dba) 2 -CuI combination catalysis in DMF, providing novel stereodefined vinylsilanes bearing an allenyl group β to silicon with cis-disposition in good yields.

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Organo-silicon compounds S 0060 Stereospecific Synthesis of a Family of Novel (E)-2-Aryl-1-silylalka-1,4-dienes (III) or (E)-4-Aryl-5-silylpenta-1,2,4-trienes (VI) via a Cross-Coupling of (Z)-Silyl-(stannyl)ethenes with Allyl Halides or PropargylBromide. -(SASAKI, F.; ENDO, T.; NOGUCHI, M.; KAWAI, K.; NAKANO*, T.; Appl. Organomet. Chem. 22 (2008) 2, 128-138; Dep. Mater. Chem., Tokai Univ., Numazu, Shizuoka 410-03, Japan; Eng.) -Mischke 29-168