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Selective Synthesis of Pyrrolidin-2-ones and 3-Iodopyrroles via the Ring Contraction and Deformylative Functionalization of Piperidine Derivatives

Abstract

In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using specific oxidant and additive.

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Publication details

The article was received on 25 Oct 2018, accepted on 03 Dec 2018 and first published on 04 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02640H
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Selective Synthesis of Pyrrolidin-2-ones and 3-Iodopyrroles via the Ring Contraction and Deformylative Functionalization of Piperidine Derivatives

    F. Wang, X. Zhang, H. Yan and X. Fan, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB02640H

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