Visible-light induced enhancement in the multi-catalytic activity of sulfated carbon dots for aerobic carbon-carbon bond formation

Abstract

The development of carbonaceous materials as metal-free catalysts integrating different types of catalysis in a single system represents a significant advance in cascade/tandem organic synthesis. Zero-dimensional carbon dots with tuneable optical properties and easily modifiable surface functionalities can be harnessed as a carbocatalyst for merging photooxidation and acid-catalyzed reactions in one pot. Herein, we explore carbon dots decorated with hydrogen sulfate groups as a photocatalyst for the dehydrogenative cross-coupling of xanthenes with ketones, arenes and 1,3-dicarbonyl compounds that showed high efficiency and selectivity under visible-light irradiation. The sulphated carbon dots demonstrate dual catalytic properties, wherein they induced the rapid photooxidation of xanthenes in the presence of molecular oxygen to form a hydroperoxy intermediate followed by coupling of nucleophiles catalysed by the acidic surface functional groups. The methodology represents an operationally simple pathway for the generation of C-C coupling products in a short reaction time with wide substrate scopes under mild conditions. The catalyst is easily separable and can be reused over multiple cycles with good efficiency. © 2019 The Royal Society of Chemistry.