Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 23, Pages 12682-12690Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02491
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Funding
- National Science Foundation of China [21472136]
- Tianjin Research Program of Application Foundation and Advanced Technology [15JCZDJC32900]
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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.
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