Pd/Cu Dual Catalysis for the Oxidative Dearomatization of PyrroleDerivatives: Mechanistic Insights and Biological Studies

Herein we report dearomatization of pyrrole ring followed by rearomatization of cyclohexyl ring to obtain isoindolinone scaffold by a Pd/Cu dual catalysis approach in an atom economic way with moderate to high yield. The expected Pd/Cu catalyzed dual C(sp2)‐H activation via normal catalytic cycle ca...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-10, Vol.27 (40), p.n/a
Main Authors: Sau, Madan, Dubey, Sapana, Roy, Shreya, Sahoo, Jigyansa, Sahoo, Gokarneswar, Sepay, Nayim, Chakraborty, Sudipta, Samanta, Shubhankar, Das, Tapas
Format: Article
Language:English
Subjects:
Bioactivity
Biological activity
Catalysis
Cytotoxic study
Dual catalysis
Oxidative dearomatization
Palladium
Rearomatization
Scaffolds
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Summary:Herein we report dearomatization of pyrrole ring followed by rearomatization of cyclohexyl ring to obtain isoindolinone scaffold by a Pd/Cu dual catalysis approach in an atom economic way with moderate to high yield. The expected Pd/Cu catalyzed dual C(sp2)‐H activation via normal catalytic cycle can be override by unusual oxidative dearomatization reaction which has been established by DFT calculation. The biological importance of isoindolinone scaffold insists us to successfully investigate in vitro antileishmanial activity of L.Donovani. We have reported an oxidative dearoamatization of pyrrole derivatives to give a highly functionalized isoindolinone derivatives. Synthesized products have been analyzed for their non‐cytotoxic behavior and two of them have been utilized for their antipromastigotic activity against L. Donovanai. In addition to that the mechanism has also been explored using DFT calculations.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400626