Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4-Addition of Zinc-Based Silicon Nucleophiles

A copper-catalyzed conjugate silylation of various cyclobutenone derivatives with Me2PhSiZnCl . 2LiCl or (Me2PhSi)(2)Zn . xLiCl (x <= 4) to generate beta-silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)(2) affords silylated enol phosphates that can be further engaged in Kumada cross-coupling reactions to yield silylated cyclobutene derivatives.

Automated summary

A copper-catalyzed method for introducing a silicon group into cyclobutenone derivatives to produce beta-silylated cyclobutanones is reported. By trapping the enolate intermediate with ClP(O)(OPh)2, silylated enol phosphates are obtained and can be further utilized in Kumada cross-coupling reactions to yield silylated cyclobutene derivatives.