Synthesis of CF3-Containing Linear Nitriles from α-(Trifluoromethyl)styrenes

Four unprecedented base-catalyzed/mediated nucleophilic additions of TMSCN to alpha-(trifluoromethyl)styrenes and 2-trifluoromethyl enynes were developed. The reaction proceeded smoothly at room temperature under mild and transition-metal-free conditions without affecting the trifluoromethyl group and afforded the corresponding CF3-containing alkyl, alkynyl, and butadienyl nitriles in moderate to excellent yields in a highly regioselective manner, respectively.

Automated summary

Four unprecedented base-catalyzed/mediated nucleophilic additions of TMSCN to alpha-(trifluoromethyl)styrenes and 2-trifluoromethyl enynes have been developed. The reaction proceeds smoothly at room temperature under mild and transition-metal-free conditions, affording the corresponding CF3-containing alkyl, alkynyl, and butadienyl nitriles in a highly regioselective manner with moderate to excellent yields.