A macrocycle-based new organometallic nano-vessel towards sustainable C2-selective arylation of free indole in water

Abstract

C2-selectivity of unsubstituted indole over facile C3-substitution is attempted by utilizing the π-cavity of a nano-vessel made up of a palladium complex of an amino-ether heteroditopic macrocycle. Functional group tolerance (cyano, nitro, halo, ester, etc.), a broad substrate scope and outstanding selectivities with excellent yields (80–93%) of the desired products have been achieved in 12 h by maintaining all sustainable conditions like aqueous medium, recyclable catalyst, one-pot reaction, no external additives, mild temperature, etc. Interestingly, we observed that electron-deficient indole derivatives underwent the present transformation with marginally superior reactivity in comparison with electron-rich indole derivatives. This approach establishes a green pathway for selective C–C coupling employing a π-cavitand as a nano-reactor.