Divergent Coupling of 2-Aryl-1,3-Indandiones with Alkenes Enabled by Iodine Catalyst

Herein, we report an iodine-catalyzed protocol for cross-coupling of 2-aryl-1,3-indandiones with alkenes. Divergent reactivity was achieved in the transformation by varying additives and solvents, thus allowing selective access to tertiary alkylated ketones and alkenes. The present approach features commercially available starting materials, broad substrate scope, general functional-group (including halogen, ester, nitrile, thioether) tolerance. Furthermore, we proposed plausible pathways to rationalize the divergent selectivity through preliminary mechanism study.

Automated summary

In this study, we developed an iodine-catalyzed protocol for the cross-coupling of 2-aryl-1,3-indandiones with alkenes. By varying additives and solvents, we achieved divergent reactivity, leading to the selective synthesis of tertiary alkylated ketones and alkenes. This approach features commercially available starting materials, broad substrate scope, and good tolerance towards various functional groups (including halogens, esters, nitriles, and thioethers). Furthermore, we proposed plausible pathways to explain the divergent selectivity through preliminary mechanism studies.