Late-stage diversification by rutheniumelectro-catalyzed C–H mono- and di-acyloxylation

Abstract

A ruthenium-catalyzed electrochemical dehydrogenative C(sp2)−H acyloxylation of aniline derivatives with carboxylic acids has been developed. Electric current is used to recycle the active ruthenium-based catalyst and promote H2 evolution. This method significantly expands the scope and enhances the selectivity of metal-electron catalyzed mono- and di-acyloxylations, which remain challenged. Our findings allowed mono-selectivity in broadly effective late-stage diversification of structurally complex drugs and natural product molecules, tolerating drugs, natural products and amino acids. The method and its underlying strategy are expected to have widespread uses in functional aniline synthesis and drug discovery process.

Keywords

• C–H activation
• Mono- and di-acyloxylation
• Ruthenium
• Electrochemistry
• Late-stage diversification