Halotrifluoromethylation of 1,3-Enynes: Access to Tetrasubstituted Allenes

A highly regioselective copper-catalyzed 1,4-chloro-and bromotrifluoromethylation of 1,3-enynes has been presented for the first time, which affords an efficient transformation to access halo- and CF3-containing tetrasubstituted allene derivatives with good to excellent yield. This protocol is practical and convenient, in which a wide range of functional groups are compatible. Applications of this method for the gram-scale preparation and late-stage functionalization of biologically active molecules are also demonstrated.

Automated summary

A highly regioselective copper-catalyzed reaction has been developed for the first time to access tetrasubstituted allene derivatives containing halogen and CF3 groups with good to excellent yields. This practical and convenient method is compatible with a wide range of functional groups and has shown promising applications in the gram-scale preparation and late-stage functionalization of biologically active molecules.