Affiliation:
1. Green Catalysis Center, and College of Chemistry Henan Institute of Advanced Technology Zhengzhou University 450001 Zhengzhou China
2. Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences) Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Lingling Road 200032 Shanghai China
Abstract
AbstractA straightforward method for the synthesis of difluoroalkylated bicyclopentanes (BCPs) from [1.1.1]propellane (TCP) through a stepwise procedure has been developed. This process involves nucleophilic addition of organozinc or ArMgBr reagents to TCP, followed by reaction with difluorocarbene to generate BCP substituted difluoroalkylzinc species, which subsequently couple with electrophiles, including allyl/propargyl bromides, (hetero)aryl disulfides, and proton, to provide a wide range of difluoroalkylated BCPs that otherwise are difficult to access through conventional methods. The transformations of the resulting products demonstrate the synthetic utility of this modular synthesis.
Funder
National Natural Science Foundation of China
Science and Technology Commission of Shanghai Municipality