Photo‐Induced Functionalization of para‐Benzoquinones: Access to Dihydroquinoxalines with a Tetrasubstituted Carbon Stereocenter. Issue 6 (14th March 2023)

• Record Type: Journal Article
• Authors: Dixit, Vikas; Sharma, Arun; Jangid, Aditya; Jain, Nidhi
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 6(2023)
• Page Start: 892
• Page End: 899
• Publication Date: 2023-03-14
• Subjects: visible light -- tetrasubstituted carbon stereocenter -- photocatalyst-free -- dihydroquinoxaline -- para-benzoquinone; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202300016
• Languages: English
• ISSNs: 1615-4150

Abstract

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.