title: Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups.
abstract: Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under Rh(III) -catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.
authors.affiliation: Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon 305-701 (Korea).|Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701 (Korea).
authors.forename: Donghyeon
authors.initials: D
authors.lastname: Gwon
authors.affiliation: Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon 305-701 (Korea).|Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701 (Korea).
authors.forename: Heejun
authors.initials: H
authors.lastname: Hwang
authors.affiliation: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400 (USA).
authors.forename: Hye Kyung
authors.initials: HK
authors.lastname: Kim
authors.affiliation: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400 (USA).
authors.forename: Seth R
authors.initials: SR
authors.lastname: Marder
authors.affiliation: Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon 305-701 (Korea). sbchang@kaist.ac.kr.|Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701 (Korea). sbchang@kaist.ac.kr.
authors.forename: Sukbok
authors.initials: S
authors.lastname: Chang
keywords: 8-aminoquinolines; CH activation; amidating reagents; carbamates; homogeneous catalysis; rhodium