Advances in cycloaddition and hydroaddition reaction of α-(trifluoromethyl)styrenes without defluorination: An alternative approach to CF3-containing compounds

alpha-(Trifluoromethyl)styrene and its derivatives have found wide applications in the fields of pharmaceuticals, agrochemicals, and advanced materials. They are also versatile trifluoromethyl-containing building blocks for the preparation of various trifluoromethyl-containing, fluorine-containing or nonfluorinated compounds. Recently, great efforts have been made to develop diverse reactions for rapidly accessing a wide range of valuable gem-difluoroalkenes and gem-difluoroalkylated compounds via defluorinative reaction or the defluorinative ipso-functionalization reaction of alpha-(trifluoromethyl)styrenes, respectively. In contrast, alpha-(trifluoromethyl)styrenes remain notably underdeveloped with respect to their use in cycloaddition and hydroaddition reaction with retaining of three C-F bonds. This short review herein is aimed to summarize the recent progress on the cycloaddition and hydroaddition reaction including nucleophilic, radical and transition metal-catalyzed addition of alpha-(trifluoromethyl)styrenes without accompanying defluorination. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

Alpha-(trifluoromethyl)styrene and its derivatives are widely used in pharmaceuticals, agrochemicals, and advanced materials. They are versatile building blocks for the preparation of various compounds. Recent efforts have focused on developing reactions for accessing gem-difluoroalkenes and gem-difluoroalkylated compounds without defluorination. However, the use of alpha-(trifluoromethyl)styrenes in cycloaddition and hydroaddition reactions while retaining three C-F bonds remains underdeveloped.