Mechanism and Scope of the Mn III ‐Initiated Oxidation of β‐Ketocarbonyl Compounds: Furan Synthesis

Unless the Mn III ‐produced carbon‐radical from β‐ketocarbonyl compounds undergoes smooth intramolecular addition to alkenes, it traps molecular oxygen in the reaction medium to produce a peroxy radical, which reacts with the neighbouring carbonyl group to form 1,2‐dioxetane. Thermal decomposition o...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-12, Vol.2012 (35), p.6976-6985
Main Authors: Wang, Chao, Li, Zhilong, Ju, Yeming, Koo, Sangho
Format: Article
Language:English
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Summary:Unless the Mn III ‐produced carbon‐radical from β‐ketocarbonyl compounds undergoes smooth intramolecular addition to alkenes, it traps molecular oxygen in the reaction medium to produce a peroxy radical, which reacts with the neighbouring carbonyl group to form 1,2‐dioxetane. Thermal decomposition of 1,2‐dioxetane completes the oxidation to produce α‐oxo ester. This oxidation seems to be general at 50 °C under aerobic conditions, and can be catalytic for Mn III in AcOH with ultrasonic irradiation. Thus, the development of a new synthetic method for diversely substituted furans has been accomplished based on a couple of the Mn III ‐initiated domino oxidation of β‐ketocarbonyl compounds with a suitable α‐allylic substitution.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201194