Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 24, Pages 12247-12257Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02176
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- CSIR, New Delhi [02(0229)/15/EMR-II]
- Indian Institute of Technology (IIT) Patna
- IIT Patna
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A straightforward method is developed in this paper for the synthesis of alpha-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-alpha-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)H (C = O) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.
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