B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
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DOI：
10.1002/adsc.201801447
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发表时间：
2019-05-14
影响因子：
5.4
通讯作者：
Xiao, Jianliang
中科院分区：
文献类型：
--
作者：
Pan, Yixiao;Luo, Zhenli;Xiao, Jianliang
报道了在温和反应条件下，以易接近且稳定的氨硼烷（AB）为还原剂，首次实现了B(C6F5)(3)催化酰胺脱氧还原成相应胺的反应。这种无金属的方案提供了方便的途径，以良好到优异的收率获得广泛的结构多样的胺产品，各种官能团，包括那些还原敏感的耐受性良好。这种新方法也适用于手性酰胺底物，而不影响对映体的纯度。在该反应中，BF3OEt2助催化剂的作用是通过原位形成酰胺-硼加合物来激活酰胺羰基。
The first B(C6F5)(3)-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the insitu formation of an amide-boron adduct.