Electrosynthesis of symmetric and highly conjugated benzofuran via a unique ECECCC electrochemical mechanism: evidence for predominance of electrochemical oxidation versus intramolecular cyclization.
Electrochemical oxidation of hydroquinone, catechol, and some of their monosubstituted derivatives has been studied in the presence of 3-hydroxy-1H-phenalen-1-one (2) as a nucleophile in water/acetonitrile (80/20) solutions using cyclic voltammetry and controlled-potential coulometry methods. The results revealed that quinones derived from oxidation of hydroquinones and catechols participate in Michael addition reactions with 2. The formed adducts convert to the corresponding benzofuran derivatives via different mechanisms. In this work, we derived a variety of products with good yields using controlled potential electrochemical oxidation at a graphite electrode in an undivided cell.
Nematollahi
Davood
D
Faculty of Chemistry, University of Bu-Ali-Sina, Hamadan, 65174, Iran. nemat@basu.ac.ir
Amani
Amene
A
Tammari
Esmail
E
D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D004563:Electrochemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001572:Benzofurans; C105430:benzofuran