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苄基是有机合成中非常常见的一类氧和氨基保护基,作为保护基我们当然希望它既能容易上,也能容易脱除保护。然而在现实的有机实验例子中,存在很多苄基通过氢解难以轻易脱除的例子(图1)。
图1:苄基氢解难脱除例子。图片来源:Synthetic Communications
来自美国的Li等人于2006年报道了将等摩尔的Pd(OH)2/C和Pd/C混合脱苄基的例子,从对比试验我们可以看出混合催化剂的脱苄基效率明显高于单独使用Pd(OH)2/C和Pd/C,不管是反应时间缩短方面,还是产率方面都有非常优秀的表现(图2和图3)。因此,大家在实验中遇到单一Pd(OH)2或C和Pd/C难以脱除的例子,可以尝试一下这个催化剂组合。
图2:芳基和烷基醚脱苄。图片来源:Synthetic Communications
图3:芳基和烷基苄胺脱苄。图片来源:Synthetic Communications
参考文献: More Efficient Palladium Catalyst for Hydrogenolysis of Benzyl Groups, Synthetic Communications, 2006, 36, 925–928.
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