Arylseleninic acid as a green, bench-stable selenylating agent: synthesis of selanylanilines and 3-selanylindoles
Laura Abenante, Nathalia B. Padilha, João M. Anghinoni, Filipe Penteado, Ornelio Rosati, Claudio Santi, Márcio S. Silva, Eder J. Lenardão
Abstract
Arylseleninic acids were used as an electrophilic selenium source in aromatic substitution reactions, using N,N-substituted anilines and indoles as nucleophiles at 70 °C for 6-15 h. A total of fourteen 4-selanylanilines and five 3-selanylindoles were selectively obtained in good to excellent yields. The starting benzeneseleninic acids are easily prepared from the respective diselenides, are bench stable and easy to handle, affording water as the only waste at the end of the reaction.
Topics & Concepts
Bench to bedsideChemistryCombinatorial chemistryMedicineMedical physicsOrganoselenium and organotellurium chemistryVanadium and Halogenation ChemistrySulfur-Based Synthesis Techniques