Raney Nickel Catalyzed Highly Chemoselective Hydrogenation for Synthesis of Tetrahydroquinolines and Indolines in
Yang Chen1, Eman Fayad2, Dalal Nasser Binjawhar3
1School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan, China.
Abstract:
The selective hydrogenation of privileged heterocycles with earth-abundant metal catalysts remains a significant yet practically important challenge in heterogeneous catalysis. Herein, we report a simple and efficient Raney nickel-catalyzed protocol for the selective hydrogenation of quinolines and indoles, delivering isolated yields of up to 99%. The practical utility of the method was further demonstrated through successful gram-scale transformations, and its use of a green solvent, an inexpensive catalyst, and operationally simple conditions affords a robust and sustainable approach for scalable heterocycle hydrogenation.
More Related Videos
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 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.
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...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.


