jo6b02176_si_001.pdf (2.44 MB)
Copper(II)-Catalyzed Benzylic C(sp3)–H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters
journal contribution
posted on 2016-11-09, 00:00 authored by Yogesh Kumar, Yogesh Jaiswal, Amit KumarA straightforward method is developed
in this paper for the synthesis
of α-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-α-ketoesters from arylacetimidates through the aerobic
oxidation of a benzylic C(sp3)–H (CO) 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.