Copper-Catalyzed Synthesis of α-Trifluoromethylacrylates from Trifluoroborylacrylates via Stereoretentive Radical Trifluoromethylation

We report the synthesis of alpha-trifluoromethylacrylates from alpha-trifluoroborylacrylatesviaa stereoretentive radical trifluoromethylation with inexpensive reagents NaSO(2)CF(3)and TBHP at room temperature. Under these conditions, a wide substrate scope afforded the (E)-diastereomer exclusively in moderate to good yield. The utility of the reaction products is demonstrated in the synthesis of phenyl-4H-pyran, a potent and selective class of IKCa channel blockers.

Automated summary

The synthesis of alpha-trifluoromethylacrylates from alpha-trifluoroborylacrylates via stereoretentive radical trifluoromethylation at room temperature using inexpensive reagents NaSO(2)CF(3) and TBHP resulted in the exclusive formation of the (E)-diastereomer in moderate to good yield. The reaction products were demonstrated to be useful in the synthesis of phenyl-4H-pyran, a potent and selective class of IKCa channel blockers.