Selective hydrogenation through phosphazide formation
Takahiro Yasuda1, Suguru Yoshida1
1Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science 6-3-1 Niijuku, Katsushika-ku Tokyo 125-8585 Japan s-yoshida@rs.tus.ac.jp.
Abstract:
The selective hydrogenation of ketones without any reaction at the azide moiety is disclosed. A key factor in the success of the reaction is the formation of phosphazides and catalyst poisoning. Hydrogenation of various functional groups was achieved in the presence of phosphazide moieties, allowing us to prepare various azides despite their significant reactivity.
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview


![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)