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

Jun Xu, Zhao-Cheng Yan, Li Liu, Long Qin, Xuan Fan, Yu Zou, Qi Zhang () and Hua-Jian Xu ()
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Jun Xu: Hefei University of Technology
Zhao-Cheng Yan: Hefei University of Technology
Li Liu: Hefei University of Technology
Long Qin: Hefei University of Technology
Xuan Fan: Hefei University of Technology
Yu Zou: Hefei University of Technology
Qi Zhang: Hefei University of Technology
Hua-Jian Xu: Hefei University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: 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 group on unsaturated C-C bonds during nucleophilic additions, preserving the pharmaceutically valuable CF2 group. Experimental data and density functional theory (DFT) calculations elucidate the regioselectivities of Cu-Bpin addition and the regulatory role of the ligand in selective deborylation processes.

Date: 2024
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DOI: 10.1038/s41467-024-51519-y

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