Applications of 2-Chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233xf): A Rapid Entry to Various β-Substituted-trifluoromethyl-ethenes.

An efficient base-promoted reaction of O-, N-, and S-nucleophiles with 2-chloro-3,3,3-trifluoprop-1-ene (HCFO-1233xf) is described providing access to various β-substituted-trifluoromethyl-ethenes under mild reaction conditions. Mechanistic investigations shed some light on the regio-, chemo-, and stereoselectivities observed. The olefins prepared represent attractive intermediates in chemical discovery: some applications include their conversion to pyrrolidines via a [3 + 2] dipolar cycloaddition reaction. These weakly basic amines represent novel synthons that could be readily elaborated through a range of reactions.