Litcius/Paper detail

Highly Enantioselective Decarboxylative Difluoromethylation

Xian Zhao, Chao Wang, Lingfeng Yin, Wei Liu

2024Journal of the American Chemical Society30 citationsDOIOpen Access PDF

Abstract

Organofluorine molecules that contain difluoromethyl groups (CF 2 H) at stereogenic centers have gained importance in pharmaceuticals due to the unique ability of CF 2 H groups to act as lipophilic hydrogen bond donors. Despite their potential, the enantioselective installation of CF 2 H groups into readily available starting materials remains a challenging and underdeveloped area. In this study, we report a nickel-catalyzed decarboxylative difluoromethylation reaction that converts alkyl carboxylic acids into difluoromethylated products with exceptional enantioselectivity. This Ni-catalyzed protocol exhibits broad functional group tolerance and is applicable for synthesizing fluorinated bioisosteres of biologically relevant molecules.

Topics & Concepts

ChemistryEnantioselective synthesisCombinatorial chemistryOrganic chemistryCatalysisFluorine in Organic ChemistryInorganic Fluorides and Related Compounds