1‐(Trifluoromethyl)cyclopent‐3‐enecarboxylic Acid Derivatives: Platforms for Bifunctional Cyclic Trifluoromethyl Building Blocks

Abstract

We report herein the synthesis and applications of 1-(trifluoromethyl)cyclopent-3-ene-1-carboxylic acid and its esters, promising new trifluoromethylated cyclic building blocks. Initially prepared starting from a pentafluorodithiopropanoic ester, a more convenient and effective approach

Olefin Metathesis Reactions with Fluorinated Substrates, Catalysts, and Solvents

“…Finally, Grellepois and Portella reported the synthesis of 1-(trifluoromethyl)cyclopentene carboxylic acid derivatives. 91 First, inspired by their own results leading to trifluoromethyl α,α-diallyl dithioesters, 92 1-(trifluoromethyl)cyclopent-3-ene carboxylic acid 152 was obtained in three steps. However, the RCM proved somewhat inefficient requiring 10 mol % of second-generation Grubbs catalyst.…”

Unique Reactivity of Fluorinated Molecules with Transition Metals

“…In 2012, Portella and coworkers developed a similar strategy for the synthesis of CF 3 -containing cyclopentenecarboxylic acid derivatives 148 as promising building blocks. [125] The derivatization of the final products would be a special feature of this work (Scheme 83).…”

Decarboxylative Allylation of Trifluoroethyl Sulfones and Approach to Difluoromethyl Compounds

“…Undeniably, the alkylation of carbanions bearing a trifluoromethyl group is one of the most difficult tasks in carbanion chemistry. Although some reactions of such carbanions have been reported, practical alkylation of trifluoroethyl carbanions and their synthetic application remain important synthetic challenges. Since our research group has recently focused on the synthetic utility of monofluoromethylated phenylsulfone derivatives such as FBSM , and FBDT, we next became interested in 2,2,2-trifluoroethyl phenylsulfones, CF 3 CHRSO 2 Ph 1 , − as precursors of trifluoroethyl carbanions CF 3 CRH – .…”