title: Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides.
abstract: Although the α-oxygenation of amines is a highly attractive method for the synthesis of amides, efficient catalysts suited to a wide range of secondary and tertiary alkyl amines using O2 as the terminal oxidant have no precedent. This report describes a novel, green α-oxygenation of a wide range of linear and cyclic secondary and tertiary amines mediated by gold nanoparticles supported on alumina (Au/Al2 O3 ). The observed catalysis was truly heterogeneous, and the catalyst could be reused. The present α-oxygenation utilizes O2 as the terminal oxidant and water as the oxygen atom source of amides. The method generates water as the only theoretical by-product, which highlights the environmentally benign nature of the present reaction. Additionally, the present α-oxygenation provides a convenient method for the synthesis of (18) O-labeled amides using H2 (18) O as the oxygen source.
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
authors.forename: Xiongjie
authors.initials: X
authors.lastname: Jin
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
authors.forename: Kengo
authors.initials: K
authors.lastname: Kataoka
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
authors.forename: Takafumi
authors.initials: T
authors.lastname: Yatabe
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
authors.forename: Kazuya
authors.initials: K
authors.lastname: Yamaguchi
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan. tmizuno@mail.ecc.u-tokyo.ac.jp.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Mizuno
keywords: amides; amines; gold; heterogeneous catalysis; α-oxygenation