Synthesis of CF3‐Substituted Olefins by Julia–Kocienski Olefination Using 2‐[(2,2,2‐Trifluoroethyl)sulfonyl]benzo[d]thiazole as Trifluoromethylation Agent

Abstract

AbstractA modified Julia–Kocienski protocol was investigated for the synthesis of CF3‐substituted terminal olefins. By employing a simple one‐step procedure, aldehydes were converted into the corresponding CF3‐substituted olefins using 2‐[(2,2,2‐trifluoroethyl)sulfonyl]benzo[d]thiazole as the trifluoromethylation agent. This sulfone was prepared on a gram scale in two steps from inexpensive and commercially available trifluoroethanol. The Julia–Kocienski olefination tolerated various functional groups, and the trifluoromethylated olefins were obtained in good yields. However, the E/Z selectivity was strongly substrate dependent, and only moderate selectivities could be achieved.