Synthesis of trans-Tetrafluoro(trifluoromethyl)-& lambda;(6)-sulfanyl (CF3SF4)-Containing Olefins via Cross Metathesis

The cross-metathesis reactions of trans-tetrafluoro(trifluoromethyl)-& lambda;(6)-sulfanyl (CF3SF4)-containing olefinsexpand the repertoire of synthetic transformations of CF3SF4-substituted molecules. Treatment of a primary alkeneand 3-CF3SF4-propene with a second-generationHoveyda-Grubbs catalyst yielded the cross-metathesis productin good yield under very mild conditions (room temperature). CF3SF4-propene undergoes cross metathesis withsubstrates containing electron-withdrawing groups or electron-donatinggroups at room temperature or under dichloromethane reflux. The formationof the CF3SF4-propene homodimer and theutility of that dimer to undergo selective cross-metathesis reactionsare described.

Automated summary

The cross-metathesis reactions of CF3SF4-substituted primary alkene and 3-CF3SF4-propene were successfully catalyzed by a second-generation Hoveyda-Grubbs catalyst under mild conditions (room temperature), resulting in good yield. CF3SF4-propene also underwent cross metathesis with substrates containing electron-withdrawing or electron-donating groups at room temperature or under dichloromethane reflux. The formation of the CF3SF4-propene homodimer and its application in selective cross-metathesis reactions were discussed.