Copper-Catalyzed Borylation and Silylation of Dichlorocyclobutenones

Abstract

We report copper-catalyzed borylation and silylation of dichlorocyclobutenones, which furnish the boron-substituted and silicon-substituted polyfunctionalized cyclobutenones in high yields. The reactions proceed under mild reaction conditions, show broad substrate scope, and display high chemoselectivity. In addition, a series of transformations of the corresponding products has been realized.

Advances in Vinyl Sulfone Catalyzed Synthesis: Methods, Mechanisms and Perspectives

“…In addition to the low price, copper catalysts typically have the advantages of low toxicity, mild chemistry and simple ligands, so catalytic systems involving copper salts are also a hot field. [42][43][44] Recently, Li and co-workers have chosen copper as the catalyst and not only demonstrated its excellent catalytic performance, but also innovatively used ethylbenzene instead of conventional alkenes and alkynes as the vinyl source to successfully construct the vinyl sulfone backbones (Scheme 3). [45] In the exploration of alkene elimination dehydrogenation, they proposed a one-pot approach to construct functionalized styrene derivatives and based on this, a series of (E)-vinyl sulfones were obtained by continuous N-sulfonylbenzo [d]imidazole in the presence of copper(I) catalyst, with a moderate to a good yield of approximately 75 %.…”

Copper-Catalyzed Regio- and Stereoselective Three-Component Coupling of Allenyl Ethers with gem-Dichlorocyclobutenones and B2pin2

“…Moreover, allene is a more challenging class of substrate in cascade reactions due to the site selectivity and other competitive reactions of gem -dichlorocyclobutenone. Inspired by previous works − and our interest in constructing C–B bonds and using gem -dichlorocyclobutenone as an electrophile to react with Cu–B/Cu–Si species to generate various boron- or silicon-substituted polyfunctionalized cyclobutenones (Scheme b), this study describes the use of gem -dichlorocyclobutenone in a copper-catalyzed three-component allylboration with allenes, which efficiently provided versatile polyfunctionalized cyclobutenones − (Scheme c).…”