Unsupported nanoporous palladium-catalyzed chemoselective hydrogenation of quinolines:Heterolytic cleavage of H2 molecule

doi:10.1016/S1872-2067(18)63151-1

Abstract

Abstract:

An efficient and highly chemoselective heterogeneous catalyst system for quinoline hydrogenation was developed using unsupported nanoporous palladium (PdNPore). The PdNPore-catalyzed chemoselective hydrogenation of quinoline proceeded smoothly under mild reaction conditions (low H₂ pressure and temperature) to yield 1,2,3,4-tetrahydroquinolines (py-THQs) in satisfactory to excellent yields. Various synthetically useful functional groups, such as halogen, hydroxyl, formyl, ethoxycarbonyl, and aminocarbonyl groups, remained intact during the quinoline hydrogenation. No palladium was leached from PdNPore during the hydrogenation reaction. Moreover, the catalyst was easily recovered and reused without any loss of catalytic activity. The results of kinetic, deuterium-hydrogen exchange, and deuterium-labeling experiments indicated that the present hydrogenation involves heterolytic H₂ splitting on the surface of the catalyst.

Key words: Nanoporous materials, Palladium, Quinolines, Chemoselective hydrogenation, Heterogeneous catalyst

Ye Lu, Yoshinori Yamamoto, Abdulrahman I. Almansour, Natarajan Arumugam, Raju Suresh Kumar, Ming Bao. Unsupported nanoporous palladium-catalyzed chemoselective hydrogenation of quinolines:Heterolytic cleavage of H₂ molecule[J]. Chinese Journal of Catalysis, 2018, 39(11): 1746-1752.

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Unsupported nanoporous palladium-catalyzed chemoselective hydrogenation of quinolines:Heterolytic cleavage of H₂ molecule

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