Palladium-catalyzed desymmetric coupling reaction between silacyclobutanes and terminal alkynes for the synthesis of silicon-stereogenic allyl vinylsilanes

Abstract

A palladium/TADDOL-derived phosphonate catalyzed desymmetric ring-opening coupling bewteen prochiral silacyclobutanes and alkyl terminal alkynes was developed. This catalytic system facilitates the formation of optically active allyl vinylsilane compounds featuring a quaternary silicon-stereogenic center, achieving good to high yields and moderate to good enantiomeric ratios. This approach significantly broaden the scope of ring-opening desymmetrization reactions involving silacyclobutanes under transition metal catalysis.

Keywords

• Silacyclobutanes
• Desymmetrization
• Palladium catalysis
• Silicon-stereogenic silanes