Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

Ling Qin (1) , Samir Z Zard (1)

1 DCSO - Laboratoire de synthèse organique

O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.

Domaines: Chimie organique

Ling Qin, Samir Z Zard. Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.. Organic Letters, 2015, 17 (6), pp.1577-80. ⟨10.1021/acs.orglett.5b00457⟩. ⟨hal-01152227⟩