A novel catalytic process for trifluoromethylation of bromoaromatic compounds

Abstract

The palladium-catalyzed trifluoromethylation of aryl bromides has been achieved in micellar media. The micellar conditions result in enhanced yields and are applicable to bromoaromatics with ketone, aldehyde, hydroxyl and amine functionalities.

Recent Developments on the Trifluoromethylation of (Hetero)Arenes

“…All the typically proposed intermediates in the catalytic cycle have been well characterized. Later on, Samant and Kabalka extended this methodology by performing the reaction in micellar media 34b. The micellar conditions increased the yields and allow the use of aryl bromides with ketone, aldehyde, hydroxy, and amine functionalities.…”

Selectivity enhancement of aromatic halogenation reactions at the micellar interface: effect of highly ionic media

“…It provides a useful reaction site to enhance the conversion and selectivity of various reactions [3]. As part of our ongoing research into selectivity improvement in organic synthesis [4][5][6][7][8][9][10][11][12], we have already described improvement in the regioselectivity of chlorination of phenol and o-chlorophenol in the presence of micelles [4]. We now present a study of selectivity enhancement in aromatic halogenation reactions.…”

Sandmeyer‐Trifluormethylierung von Aryldiazoniumtetrafluorboraten

“…[3] Aufbauend auf grundlegenden Arbeiten zu Cu-und Pd-Perfluoralkylkomplexen von McLoughlin, Yagupolskii, Burton, Chambers, Grushin und anderen wurden in letzter Zeit erhebliche Fortschritte bei der Entwicklung von Trifluormethylierungsreaktionen gemacht, die die selektive Einführung von CF 3 -Gruppen in hochfunktionalisierte Zwischenprodukte in späten Syntheseschritten ermçglichen. Grushin, [5d] Sanford [13] und Buchwald [14] entwickelten Trifluormethylierungen von Arylhalogeniden, die auf Palladium-Komplexen basieren. [5] Zur ersten gehçren Kupplungen von Arylhalogeniden mit nukleophilen CF 3 -Reagentien (b), in der Regel stçchiometrisch eingesetzte Kupfer-CF 3 -Komplexe.…”