Photo‐Induced Functionalization of <i>para</i>‐Benzoquinones: Access to Dihydroquinoxalines with a Tetrasubstituted Carbon Stereocenter
Vikas Dixit, Arun Sharma, Aditya R. Jangid, Nidhi Jain
Abstract
Visible light induced activation of para-benzoquinone, and its sequential coupling with alkynes and ortho-phenylenediamines/ortho-aminophenols is reported. The protocol provides a route for synthesizing value-added quinoxaline derivatives with tetrasubstituted carbon stereocenter at room temperature in 36–75% yields. Mechanistic investigation suggests that the reaction proceeds via in-situ generation of para-quinone methide through direct excitation of para-benzoquinone in blue light.
Topics & Concepts
StereocenterChemistryBenzoquinoneCombinatorial chemistryCarbon fibersQuinoxalineEnantioselective synthesisOrganic chemistryComputer scienceCatalysisAlgorithmComposite numberSynthesis of Indole DerivativesSynthesis and Biological EvaluationCatalytic C–H Functionalization Methods