Intramolecular Electro-Oxidative Addition of Enamines to Alkynes: Easy Access to Pyrrole-4-carbaldehydes and Ketones

Dutta, Jhilik (2022) Intramolecular Electro-Oxidative Addition of Enamines to Alkynes: Easy Access to Pyrrole-4-carbaldehydes and Ketones. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Jhilik Dutta (17MS024)) 17MS024_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (5MB)

Abstract

A transition metal-free, cost-effective, environmentally benign electrochemical approach has been developed to synthesize poly-substituted pyrrole derivatives. The synthetic strategy consists of an intramolecular oxidative addition of enamine moiety to the alkyne counterpart to achieve pyrrole-4-carbaldehyde and ketone derivatives. The electricity mediated iodide catalyzed cyclization of various alkyl- or aryl-substituted N-propargyl enamine carboxylates led to a range of substituted pyrrole-4-carbaldehyde and ketone derivatives with up to 93% yield. A deep investigation showed that the minimal amount of water present in the medium had a definitive role to convert isolated iodo-cyclized intermediate to our desired pyrrole-4-carbonyl compounds.

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