Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides

Angew Chem Int Ed Engl. 2019 Oct 14;58(42):14901-14905. doi: 10.1002/anie.201906815. Epub 2019 Sep 19.

Abstract

A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)2 ⋅4 H2 O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.

Keywords: alkenes; halides; kinetics; nickel; reaction mechanisms.