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  4. Pd/C促进的四氢异喹啉高选择性部分脱氢

催化学报 , 2015, (1): 33-39. doi: 10.1016/S1872-2067(14)60243-6

Pd/C促进的四氢异喹啉高选择性部分脱氢

姬悦 1, , 陈木旺 2, , 时磊 3, , 周永贵 4,

1.中国科学院大连化学物理研究所,辽宁大连,116023

2.中国科学院大连化学物理研究所,辽宁大连,116023

3.中国科学院大连化学物理研究所，辽宁大连116023; 大连理工大学精细化工国家重点实验室，辽宁大连116024

4.中国科学院大连化学物理研究所,辽宁大连,116023

基金项目:   大连理工大学精细化工国家重点实验室开放课题基金(KF1110)   国家自然科学基金(21202162)  

关键词： 钯碳 , 部分脱氢 , 四氢异喹啉 , 亚胺 , 脱氢芳构化

Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

Keywords： Palladium on carbon , Partial dehydrogenation , Tetrahydroisoquinoline , Imine , Dehydroaromatization

采用K3PO4×3H2O修饰的Pd/C为催化剂实现了取代四氢异喹啉高选择性部分脱氢,并成功地避免了当量有害氧化剂的使用。多相催化剂Pd/C对四氢异喹啉化合物具有催化脱氢活性,但反应选择性较差,同时产生完全脱氢的芳构化产物异喹啉。而K3PO4×3H2O修饰的Pd/C催化剂能有效提高脱氢反应的化学选择性,在最优条件下可获得最高89%的分离收率。这为取代3,4-二氢异喹啉的合成提供了一种简便、高原子经济性和高化学选择性的反应途径。此外,该多相催化剂可回收循环使用多次,且活性和选择性基本保持不变。

A highly selective procedure has been developed for the partial dehydrogenation of 1‐substitut‐ed‐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‐dihy‐droisoquinolines 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 dehydroaromatiza‐tion. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improve‐ments 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 practi‐cal potential of this methodology.

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