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

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

Org Biomol Chem

School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S.C. Mullick Road, Kolkata 700032, India.

Published: September 2024

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, .), 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, . 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.

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http://dx.doi.org/10.1039/d4ob00886cDOI Listing

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