Iodine(III)-Mediated Migratory gem-Difluorinations: Synthesis of β Transformable Functionality Substituted gem-Difluoroalkanes

Abstract

Geminal-difluoroalkanes featuring intriguing steric and electronic properties are of great significance in medicinal chemistry, and great progresses have been achieved for their synthesis. In recent years, iodine(III) reagent-mediated migratory gem-difluorination of alkenes has proved to be an efficient and powerful strategy to access to diverse gem-difluoroalkanes, especially those bearing a readily transformable functionality (TF), which are important for rapid assembly of complex gem-difluorinated molecules in a modular and diverse manner. In this review, we systematically summarize the recent development of iodine(III)-mediated migratory gem-difluorination reactions for the synthesis of gem-difluoroalkanes bearing a synthetically versatile TF at the β position. The reaction mechanism and the utilities of the products are also discussed. This review is presented and grouped basically according to the types of transformable functionalities within the products.

Keywords: gem-difluorination; gem-difluoroalkane; iodine(III) reagent; migratory reaction; transformable functionality.