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Diisobutylaluminum borohydride: An efficient reagent for the reduction of tertiary amides to the corresponding amines under ambient conditions
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2017-09-18 , DOI: 10.1016/j.tetlet.2017.09.030
Rachel A. Snelling , Gabriella Amberchan , Angel Resendez , Chris L. Murphy , Lauren Porter , Bakthan Singaram

A synthetically simple mixed metal hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], is easily generated from a 1:1 mixture of borane-dimethylsulfide (BMS) and diisobutylaluminum hydride (DIBAL). The reduction of tertiary amides using (iBu)2AlBH4 is complete within five minutes under ambient conditions and the product tertiary amines were isolated in 70–99% yields by a simple acid-base extraction. This new methodology, reported herein, works well for reduction of tertiary aliphatic and aromatic amides as well as lactams to the corresponding amines and product isolation and purification does not require column chromatography.



中文翻译:

二异丁基硼氢化铝:一种在环境条件下将叔酰胺还原为相应胺的有效试剂

合成简单的混合金属氢化物二异丁基硼氢化铝[(i Bu)2 AlBH 4 ]易于从硼烷-二甲基硫醚(BMS)和二异丁基氢化铝(DIBAL)的1:1混合物中生成。在环境条件下,使用(i Bu)2 AlBH 4可以在五分钟内完成叔酰胺的还原,并且可以通过简单的酸碱萃取以70-99%的产率分离出叔胺产物。本文报道的这种新方法学非常适用于将脂族和芳族叔酰胺以及内酰胺还原为相应的胺,并且产物的分离和纯化不需要柱色谱法。

更新日期:2017-09-18
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