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TBHP/TBAI-Mediated Oxidative Cascade Reaction Consisting of Dimerization, Cyclization, and 1,2-Aryl Migration: Metal-Free Synthesis of Pyrrolin-4-ones and Highly Substituted Pyrroles

TBHP/TBAI-Mediated Oxidative Cascade Reaction Consisting of Dimerization, Cyclization, and 1,2-Aryl Migration: Metal-Free Synthesis of Pyrrolin-4-ones and Highly Substituted Pyrroles

Xiaoyuan Zhao, Yong Zhang, Jun Deng, Daisy Zhang-Negrerie, Yunfei Du

J Org Chem. 2017 Dec 1;82(23):12682-12690.

PMID: 29045795

Abstract:

Treatment of enamino esters with TBHP (t-butylhydroperoxide) and TBAI (t-butylammonium iodide) in HFIP (hexafluoroisopropanol) was found to afford a variety of substituted pyrrolin-4-one compounds. This metal-free oxidative cascade reaction consists of the key steps of coupling of two radical intermediates, an intramolecular ring closure, and an exclusive 1,2-aryl radical migration. Upon treatment with a base, the obtained pyrrolin-4-ones could be converted to the highly substituted pyrrole compounds.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP39557454	t-Butylammonium iodide		39557-45-4	Price

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