Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

Abstract

As a consequence of the expanding relevance of fluorine-containing organic molecules in drug research, the synthesis of organofluorine scaffolds has received high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon–carbon multiple bonds, with the simultaneous introduction of a CF3 group and another function, have considerable potential. Considering the high importance of carbon–carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, alkynyltrifluoromethylations are considered to be increasing areas of synthetic chemistry. Alkynyltrifluoromethylation is a narrow segment and a relatively new approach in synthetic chemistry, however it has not been reviewed so far. Therefore, our goal in the current minireview is to summarize the recent developments of alkynyltrifluoromethylation reactions taking into consideration several main aspects, such as (a) alkynyltrifluoromethylation reactions of alkenes including (i) reactions involving intramolecular alkynyl migration and (ii) intermolecular transformations as well as (b) alkynyltrifluoromethylation reactions of alkynes.

Palladium-Catalyzed 1,1-Alkynyloxygenation of 2-Vinylbenzoates with Alkynyl Bromides

“…In this reaction, the scope of the carbon functionalities that can be introduced is limited to an alkenyl moiety. The introduction of an alkyne in this 1,1-carbooxygenation reaction would serve as a valuable method in view of the synthetic utility of an alkyne functionality, including as a component in click reactions. , We report herein on the Pd-catalyzed 1,1-alkynyloxygenation of 2-vinylbenzoates using alkynyl bromides, leading to the formation of 3-alkynylated isochroman-1-ones (Scheme c) …”