Siva Reddy A, Ranjith Reddy K, Nageswar Rao D, Jaladanki Chaitanya K, Bharatam Prasad V, Lam Patrick Y S, Das Parthasarathi
Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.
Department of Medicinal Chemistry, National Institute of Educational and Research (NIPER), S.A.S Nagar, Mohali, Punjab-160062, India.
Org Biomol Chem. 2017 Jan 25;15(4):801-806. doi: 10.1039/c6ob02444k.
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.
已开发出铜（II）催化的硼酸促进的未保护氨基酚的化学选择性N-芳基化反应。在室温下，使用Cu（OAc）/AgOAc组合在甲醇中可实现3-氨基酚的选择性N-芳基化，而使用Cu（OAc）/CsCO体系并以苯甲酸作为添加剂可获得4-氨基酚的化学选择性N-芳基化产物。这些无配体条件和“开放式烧瓶”化学方法具有很强的适应性，与多种官能团兼容。通过考虑密度泛函理论（DFT）计算对这种选择性N-芳基化反应进行了机理研究。
