Metal‐free Catalytic Esterification of Aryl Alkyl Ketones with Alcohols via Free‐radical Mediated C(sp3)−H Bond Oxygenation

A novel metal‐free catalytic one‐pot approach has been developed for the esterification of aralkyl ketones with alcohols under open‐air atmospheric conditions. The inexpensive iodide/oxone reagent system allowed the cascade C(sp3)−H bond oxygenation, selective C−C bond cleavage and esterification th...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-03, Vol.10 (3), p.594-601
Main Authors: Rammurthy, Banothu, Peraka, Swamy, Vasu, Amrutham, Krishna Sai, Gajula, Divya Rohini, Yennamaneni, Narender, Nama
Format: Article
Language:English
Subjects:
Alcohols
Benzoates
C−C Bond cleavage
Esterification
Functional groups
Hydrogen bonds
Ketones
Organic chemistry
Oxidation
Oxygenation
Reagents
Redox Iodine Catalysis
Regioselectivity
Selectivity
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Summary:A novel metal‐free catalytic one‐pot approach has been developed for the esterification of aralkyl ketones with alcohols under open‐air atmospheric conditions. The inexpensive iodide/oxone reagent system allowed the cascade C(sp3)−H bond oxygenation, selective C−C bond cleavage and esterification through the both radical and ionic pathways in a stepwise manner in one‐pot. This mild, convenient and economically viable catalytic method tolerates the various functional groups to provide the corresponding alkyl benzoates in up to 98% yields with up to 99% selectivity. The efficiency and feasibility of scale‐up of the present catalytic system was demonstrated with gram scale experiments (up to 10 gram scale). An unprecedented metal‐free catalytic protocol for the esterification of aryl alkyl ketones with alcohols in one‐pot cascade manner using eco‐friendly reagents has been developed.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202000691