Zinc-Enabled Annulation of Trifluorodiazoethane with 2H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines

Chen, Yue-Ji; Zhang, Fa-Guang; Ma, Jun-An

Zinc-Enabled Annulation of Trifluorodiazoethane with 2H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines

2021

Chen, Yue-Ji | Zhang, Fa-Guang | Ma, Jun-An

A diethylzinc-promoted unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines is described. This transformation involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, thus giving a broad array of 3-trifluoromethyl pyrazolines in good yields with excellent diastereoselectivities. Further transformations provide facile access to 3-trifluoromethyl pyrazoles and 3,5-ditrifluoromethyl pyridazines with good efficiency.

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