DOI: 10.1021/acs.orglett.6c02930 ISSN: 1523-7060

Diboron-Enabled Nickel-Catalyzed Reductive Hydroperfluoroalkylation toward β-Perfluoroalkyl Carbonyls

Lili Zhao, Chenyang Liu, Jiaming Li, Yanli Yuan, Xiaojun Zeng

Abstract

Carbonyl compounds serve as versatile building blocks in medicine chemistry. The hydroperfluoroalkylation of unsaturated carbonyl compounds offers a powerful strategy for introducing valuable fluorine-containing motifs into drug-like molecules. Herein, we report a diboron-enabled Ni catalytic system for the unified and highly regioselective reductive hydroperfluoroalkylation of unsaturated carbonyl compounds. This protocol efficiently incorporates diverse perfluoroalkyl groups into amides, ketones, and esters under mild conditions, delivering β-perfluoroalkyl products in good to excellent yields. This method provides a practical, route to synthetically useful fluorinated building blocks.

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