title: Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols.
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/Cs2CO3system 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.
authors.affiliation: Medicinal 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.
authors.forename: A
authors.initials: A
authors.lastname: Siva Reddy
authors.affiliation: Medicinal 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.
authors.forename: K
authors.initials: K
authors.lastname: Ranjith Reddy
authors.affiliation: Medicinal 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.
authors.forename: D
authors.initials: D
authors.lastname: Nageswar Rao
authors.affiliation: Department of Medicinal Chemistry, National Institute of Educational and Research (NIPER), S.A.S Nagar, Mohali, Punjab-160062, India.
authors.forename: Chaitanya K
authors.initials: CK
authors.lastname: Jaladanki
authors.affiliation: Department of Medicinal Chemistry, National Institute of Educational and Research (NIPER), S.A.S Nagar, Mohali, Punjab-160062, India.
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
authors.affiliation: Baruch S. Blumberg Institute, 3805 Old Easton Road, Doylestown, PA 18902, USA.
authors.forename: Patrick Y S
authors.initials: PY
authors.lastname: Lam
authors.affiliation: Medicinal 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.
authors.forename: Parthasarathi
authors.identifier: http://orcid.org/0000-0002-9306-4956
authors.initials: P
authors.lastname: Das