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Oxidative Coupling of 4‐Hydroxycoumarins with Quinoxalin‐2(1H)‐ones Induced by Visible Light under Aerobic Conditions

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A green protocol was developed for the cross-dehydrogenative coupling of quinoxalin-2-ones and 2-hydroxycoumarin derivatives, only using the Fukuzumi photocatalyst and visible light to obtain hybrid drug-like molecules in a single step.


Abstract

Direct and selective C(sp2)−H/C(sp2)−H cross-dehydrogenative coupling has become a promising strategy to increase molecular complexity with a high atom economy. This study describes an efficient and straightforward protocol for the regioselective C3-H/C3-H cross-coupling of 4-hydroxycoumarin derivatives with quinoxalin-2(1H)-ones, including late-stage modification of natural drugs, promoted by visible light under aerobic conditions at room temperature. With this approach, a wide range of hybrid drug-like molecules were prepared, using air as the terminal oxidant. Remarkably, the C4-OH group at the coumarin ring is essential for the reaction and has been used as a handle for diverse functionalizations of the final products. Moreover, sunlight can promote the reaction under very mild and sustainable conditions, even on a gram scale. Qualitative and semi-quantitative tools were used to demonstrate the greenness advance of this methodology over previously reported ones. Several experiments were conducted to propose a plausible mechanism for this transformation.

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