Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO2F2)

Xian-Lin Chen; Hua-Li Qin

doi:10.3762/bjoc.19.68

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO₂F₂)

Beilstein J Org Chem. 2023 Jun 22:19:901-908. doi: 10.3762/bjoc.19.68. eCollection 2023.

Authors

Xian-Lin Chen^#¹, Hua-Li Qin^#¹

Affiliation

¹ School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, PR China.

^# Contributed equally.

Abstract

A SO₂F₂-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.

Keywords: E-selectivity; SO2F2; direct N–O activation; nitrile synthesis; ring-opening cross-coupling; sulfuryl fluoride.

Grants and funding

We are grateful to the National Natural Science Foundation of China (Grant No. 22071190) and Wuhan University of Technology for the financial support.