Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols.

Org Biomol Chem

Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India. and Academy of Scientific and Innovative Research (AcSIR), New Delhi-110025, India.

Published: January 2017

Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)/CsCO system and benzoic acid as an additive. These ligand-free conditions and "open-flask" chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.

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http://dx.doi.org/10.1039/c6ob02444kDOI Listing

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