Copper-catalyzed highly switchable defluoroborylation and hydrodefluorination of 1-(trifluoromethyl)alkynes.

ABSTRACT: CF₂-containing compounds hold significant potential in drug discovery, organic synthesis, and materials science. However, synthesizing various CF₂-containing building blocks from a single compound remains challenging. Here, we present a Cu-catalyzed, switchable defluoroborylation and hydrodefluorination of trifluoromethylated alkynes, yielding four types of CF₂-containing compounds. The chemo- and regio-selective sp²/sp³ 1,2-diborylation and sp² monoborylation of 1-(trifluoromethyl)alkynes are controlled by adjusting the solvent and ligand quantity. Additionally, altering the base allows selective generation of gem-difluoroalkenes or difluoromethylalkenes. Notably, our method prevents over-defluorination of the CF₃

SUBMITTER: Xu J 

PROVIDER: S-EPMC11329652 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature