Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO 2 F 2 ).

A SO 2 F 2 -mediated ring-opening cross-coupling of cyclobutanone oxime derivatives with alkenes was developed for the construction of a range of δ-olefin-containing aliphatic nitriles with ( E )-configuration selectivity. This new method features wide substrate scope, mild conditions, and direct N-O activation.