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 subst...

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Published in:Journal of organic chemistry 2024-08, Vol.89 (15), p.10462-10466
Main Authors: Karnat, Alexandre, Fouquet, Eric, Toullec, Patrick Y.
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00581