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Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols
A Siva Reddy1, K Ranjith Reddy1, D Nageswar Rao1
1Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India. partha@iiim.ac.in and Academy of Scientific and Innovative Research (AcSIR), New Delhi-110025, India.
Abstract:
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)2/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)2/Cs2CO3 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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