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Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from N-Propargyl Enamines/Amides

Mrinmay Baidya, Jhilik Dutta and Suman De Sarkar*

*Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, West Bengal, India, Email: sdsiiserkol.ac.in

M. Baidya, J. Dutta, H. D. Sarkar, Org. Lett., 2023, 25, 3812-3817.

DOI: 10.1021/acs.orglett.3c01355


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Abstract

Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes provides carbonyl-pyrroles or -oxazoles in very good yields from N-propargyl derivatives. Organoselenium played a crucial role as a π-Lewis acid and selectively activated the alkyne for the successful nucleophilic addition.

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proposed mechanism



Key Words

pyrroles, oxazoles, electrochemistry


ID: J54-Y2023