Benzisoselenazoles as Selenophenolate Anion Surrogates for the Formation of Carbon–Selenium Bonds via the Selena-Kemp Reaction

The in situ base-promoted generation of unstable selenophenolate
anions from 1,2-benzisoselenazoles via a variant of the Kemp elimination
has been developed. 2-Cyano-substituted selenophenolate anions obtained
by this methodology were engaged in nucleophilic substitution, aromatic
nucleophilic substitution, and Pd-catalyzed cross-coupling reactions
to give functionalized arylalkyl and diaryl selenides in moderate
to excellent yields.