title: Copper-Catalyzed 8-Amido Chelation-Induced Remote C-H Amination of Quinolines.
abstract: A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96%). A single-electron transfer (SET)-mediated mechanism with kH /kD =1.1 was proposed after trapping of the radical intermediate.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India.
authors.forename: Harekrishna
authors.initials: H
authors.lastname: Sahoo
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India.
authors.forename: Mallu Kesava
authors.initials: MK
authors.lastname: Reddy
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India.
authors.forename: Isai
authors.initials: I
authors.lastname: Ramakrishna
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India. mbaidya@iitm.ac.in.
authors.forename: Mahiuddin
authors.initials: M
authors.lastname: Baidya
keywords: C−H activation; amination; azo compounds; copper; homogeneous catalysis