Transition-metal-free, oxidative C(sp3)–H arylation of amides with zeolite catalysts

Abstract

The oxidative coupling of amides and heteroarenes would allow for joining two of the most privileged scaffolds in medicinal chemistry. Here, we show that zeolite catalysts in combination with tert-butylperoxy ethylhexyl carbonate (TBEC) as oxidant can improve the formation of heterocoupled products. The exceptional selectivity and high yields are attributed to a pathway proceeding by a 2-electron oxidation of the amide to an N-acyliminium cation, followed by an electrophilic attack on the heterocycle.