Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C–H Alkylation with Maleimides

An enol-assisted regioselective arene C–H alkylation with maleimides is developed under redox-neutral ruthenium­(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce s...

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Bibliographic Details
Published in:Organic letters 2023-01, Vol.25 (1), p.70-75
Main Authors: Mondal, Sudeshna, Bera, Ratnadeep, Chowdhury, Deepan, Dana, Suman, Baidya, Mahiuddin
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Maleimides
Oxidation-Reduction
Ruthenium - chemistry
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Summary:An enol-assisted regioselective arene C–H alkylation with maleimides is developed under redox-neutral ruthenium­(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C–H metalation step for this reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03858