Rh(III)‐Catalyzed Divergent C2‐carboxymethylation of Indoles and C7‐formylmethylation of Indolines with Vinylene Carbonate
Weinan Hu, Xu Wang, Xiaoni Yu, Xinju Zhu, Xin‐Qi Hao, Mao‐Ping Song
Abstract
Abstract A Rh‐catalyzed divergent alkylation of indole derivatives with vinyl carbonate was described. Depending on the substrate and solvent, indoles reacted with vinyl carbonate and alcohols to give C2 carboxymethylated adducts via a sequential three‐component reaction, while indolines reacted with vinyl carbonate in toluene to provide C7 formylmethylated products. The structures of carboxymethylated product 3 a and formylmethylated product 5 a were further confirmed by X‐ray analysis. The current protocol featured broad substrate scope, tunable reaction conditions, divergent functionalization, and good regioselectivity.
Topics & Concepts
ChemistryRegioselectivityCatalysisCarbonateSubstrate (aquarium)Indole testSurface modificationDimethyl carbonateAdductAlkylationOrganic chemistrySolventPolymer chemistryPhysical chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysisCatalytic Alkyne Reactions