Visible-Light Photoredox Catalyzed Decarboxylative Alkylation of Vinylcyclopropanes

Herein, we report a visible-light mediated photoredox catalyzed decarboxylative alkylation of vinylcyclopropanes. The reaction was carried out with an Ir-based photocatalyst and Cs2CO3 as a base. The desired functionalized long-chained alkylated derivatives were obtained in 48-93% yields under mild reaction conditions without any external metal co-catalysts, oxidants, or additives. Various alkyl carboxylic acids and amino acid derivatives are used as alkylating reagents to synthesize the gamma,delta-unsaturated diesters, and unnatural homo-allylic amino acid derivatives with excellent functional groups tolerance. The utility of this method was showcased by performing a gram-scale synthesis. A mechanism is proposed based on control experiments and quenching studies.

Automated summary

This study presents a visible-light mediated photoredox catalyzed decarboxylative alkylation of vinylcyclopropanes using an Ir-based photocatalyst and Cs2CO3 as a base. Long-chained alkylated derivatives were obtained in moderate to high yields under mild reaction conditions without the need for external metal co-catalysts, oxidants, or additives. Various alkyl carboxylic acids and amino acid derivatives were used as alkylating reagents to synthesize gamma,delta-unsaturated diesters and unnatural homo-allylic amino acid derivatives with excellent functional groups tolerance. The method was further validated through gram-scale synthesis and a proposed mechanism based on control experiments and quenching studies.