Weak Coordinating Carbonyl-Directed Rhodium(III)-Catalyzed C–H Activation at the C4-Position of Indole with Allyl Alcohols
Mahadev Sharanappa Sherikar, Ravi Devarajappa, Kandikere Ramaiah Prabhu
Abstract
A weakly coordinating carbonyl-directed coupling of allyl alcohols at the C-4 position of indole derivatives under the C-H activation conditions catalyzed by Rh(III) is reported. This results in alkylation at the C-4 position of indole derivatives exclusively. The obtained product forms a tricyclic derivative under aldol reaction conditions, which can be a potential precursor for synthesizing a few alkaloid molecules such as ergot, hapalindole alkaloids, and related heterocyclic compounds.
Topics & Concepts
ChemistryIndole testRhodiumAlkylationDerivative (finance)CatalysisAldol reactionStereochemistryMedicinal chemistryOrganic chemistryFinancial economicsEconomicsCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Alkyne Reactions