Synthesis of Propargylic Fluorides toward Carbo- and Heterocycles with Mono- and gem-Difluorinated Side Chains

Abstract

International audienceThis review reports the synthesis of propargylic derivatives with alkyl chains bearing either one fluorine or a gem-difluoro system. The preparation of the different categories of fluorinated derivatives is analyzed in a systematic manner, based on the nature of substituents close to the fluorine atom(s). In the second part of this review are summarized the synthetic applications of these fluorinated propargylic intermediates, focusing mainly on the preparation of carbo- and heterocyclic derivatives. 1 Introduction 2 Synthesis of Propargylic Fluorides 3 Use of Propargylic Fluorides in the Preparation of Carbo- and Heterocycles with Fluorine-Containing Side Chains 4 Conclusions and Perspectives © Georg Thieme VerlagStuttgart · New York

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

“…Our research program aims to synthesize new fluorinated molecules based on the easy access and the versatility of fluorinated propargylic derivatives [21]. Thus, taking into account the known biological properties of the imidazo-fused N -heterocycles, we became interested in the preparation of new derivatives of this type possessing gem -difluorinated side chains as indicated in Fig.…”

Photoinduced Copper-Catalyzed Monofluoroalkylation of Terminal Alkynes to Propargylic Fluorides

“…Indeed, a variety of fluorinated compounds have been widely used in pharmaceuticals and agrochemicals, as well as in performance materials, − and thus, the increasing demand for fluorinated molecules has led to seek ingenious preparation methods. For example, propargylic fluorides serve as prevailing motifs widely found in important biological compounds, such as insecticides, fluorinated corticosteroids, fluorinated analogues of nucleosides, and fluorinated prostacyclin (Scheme a) …”