Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the ring contraction and deformylative functionalization of piperidine derivatives?

Organic & Biomolecular Chemistry Pub Date: 2018-12-04 DOI: 10.1039/C8OB02640H

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 a specific oxidant and additive.

Graphical abstract: Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the ring contraction and deformylative functionalization of piperidine derivatives
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