Citation: Yue Ji, Mu-Wang Chen, Lei Shi, Yong-Gui Zhou. Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C[J]. Chinese Journal of Catalysis, ;2015, 36(1): 33-39. doi: 10.1016/S1872-2067(14)60243-6 shu

Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

Yue Ji ^a ,
Mu-Wang Chen ^a ,
Lei Shi ^a,b,, ,
Yong-Gui Zhou ^a,,

1.
a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: Lei Shi, Yong-Gui Zhou,
Received Date: 1 October 2014
Available Online: 3 November 2014
Fund Project: 国家自然科学基金(21202162) (21202162) 大连理工大学精细化工国家重点实验室开放课题基金(KF1110). (KF1110)

A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K₃PO₄×3H₂O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K₃PO₄×3H₂O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology.
- Palladium on carbon,
- Partial dehydrogenation,
- Tetrahydroisoquinoline,
- Imine,
- Dehydroaromatization
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