Organoborane-Catalyzed Hydrogenation of Unactivated Aldehydes with a Hantzsch Ester as a Synthetic NAD(P)H Analogue
Organoborane-Catalyzed Hydrogenation of Unactivated Aldehydes with a Hantzsch Ester as a Synthetic NAD(P)H Analogue
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DOI：
10.1055/s-0034-1378846
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发表时间：
2015-09-01
期刊：
影响因子：
2
通讯作者：
Uozumi, Yasuhiro
中科院分区：
文献类型：
--
作者：
Hamasaka, Go;Tsuji, Hiroaki;Uozumi, Yasuhiro
我们开发了一种非活化醛的加氢方法，使用Hantzsch酯作为NAD(P)H类似物，在缺电子三烷基硼烷作为刘易斯酸催化剂的存在下。因此，三[3,5-二（三氟甲基）苯基]硼烷在100℃下有效地催化脂肪族醛与1,4-二恶烷中的汉茨酯加氢，以高达97%的收率生成相应的脂肪族伯醇。即使在25℃下，芳香族醛也会发生氢化反应，以高达100%的收率生成相应的芳香族伯醇。
We have developed a method for the hydrogenation of unactivated aldehydes, using a Hantzsch ester as a NAD(P)H analogue in the presence of an electron-deficient triarylborane as a Lewis acid catalyst. Thus, tris[3,5-bis(trifluoromethyl)phenyl]borane efficiently catalyzes the hydrogenation of aliphatic aldehydes with a Hantzsch ester in 1,4-dioxane at 100 degrees C to give the corresponding aliphatic primary alcohols in up to 97% yield. Aromatic aldehydes also undergo the hydrogenation, even at 25 degrees C, to furnish the corresponding aromatic primary alcohols in up to 100% yield.