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Updated: Jul 29, 2025

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Published on: June 10, 2021
Base-mediated ynone-isocyanide [3+2] cycloaddition: a general method to 2,3,4-tri-substituted 1-H-pyrroles and
Ankit Kumar1, Pawan K Mishra1, Akhilesh K Verma1
1Department of Chemistry, University of Delhi, Delhi 110007, India. averma@acbr.du.ac.in.
Abstract:
A transition-metal-free and base-promoted one-pot synthesis of 2,3,4-trisubstituted 1-H-pyrroles has been developed. The reaction occurs through the [3+2] cycloaddition of differently functionalized ynones and isocyanides. The reaction's advantageous features are operational simplicity, atom economy, and functional group tolerance with broad substrate scope. In addition, 1,3-bis-pyrrole formation and gram-scale synthesis were also achieved. Furthermore, the synthetic utility of the products was also investigated via isocyanide insertion and pyrrole-triazole hybrid formation in good yield.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.