Beilstein J. Org. Chem.2023,19, 901–908, doi:10.3762/bjoc.19.68
Xian-Lin Chen Hua-Li Qin School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, PR China 10.3762/bjoc.19.68 Abstract A SO2F2-mediated ring-openingcross-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: direct N–O activation; E-selectivity; nitrile synthesis; ring-openingcross-coupling; sulfuryl
completely inhibited when the amount of added TEMPO was increased to 2 equivalents.
Based upon the preliminary results and previous reports of this class of transformation [26][30][36][37][42][60][61], a plausible mechanism for the base-promoted, SO2F2-mediated ring-openingcross-coupling of cyclobutanone
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Graphical Abstract
Scheme 1:
Representative nitrile-containing functional materials, drug carriers, and medicines.