Concerted nucleophilic substitution reaction proceeds smoothly at sp3 atoms, while it hardly occurs at sp2 centers.
By our recent study, such a nucleophilic substitution is found to proceed at sp2 atoms of oximes, lithium carbenoids, and even vinylic halides.
In this lecture we will introduce such sp2-center substitution reactions (mostly vinylic substitution) with experimental and theoretical examples.