Affiliation:
1. State Key Laboratory of Anti-Infective Drug Discovery and Development, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University
2. Department of Hepatobiliary and Pancreatic Surgery, Hainan General Hospital; Affiliated Hainan Hospital of Hainan Medical University
Abstract
Abstract1,3-Difluorinated compounds are characterized by their unique conformation, influenced by 1,3-dipolar minimization effects. However, their synthetic methods are relatively limited. Here, a ring-opening 1,3-difluorination of benzylidenecyclopropanes (BCPs) using HF·Py, mediated by an electron-poor hypervalent iodine reagent, which is generated in situ by the oxidation of o-nitroiodobenzene with mCPBA is described. The protocol features mild reaction conditions, good functional group tolerance, and moderate to good yields. Additionally, the synthetic utility of this method is showcased by further transformations of the olefin group and allylic fluoride motif.
Funder
National Natural Science Foundation of China
Basic and Applied Basic Research Foundation of Guangdong Province
Guangdong Provincial Key Laboratory of Construction Foundation