铜催化的硅烷还原酰基叠氮的反应研究

Study on the copper-catalyzed reduction of acyl azides with hydrosilanes

本文报道了铜催化的硅烷还原酰基叠氮的反应。考察了多种CuCl_n/NHC·HCl(n=1,2;NHC=N-杂环卡宾)催化剂前体和不同的硅烷的组合体系。筛选确定了最有效率的CuCl/IPr·HCl(IPr=N,N'-双(2,6-二异丙基苯基)咪唑-2-亚基)作为催化前体和使用(EtO)_3SiH作为还原试剂为最优条件。该方法原料及催化剂廉价易得,反应条件温和,效率高。具有良好的化学选择性和官能团耐受性,能以较高的产率得到多种不同类型的甲酰胺,是还原酰基叠氮以制备甲酰胺类化合物的高效的新方法。所有的产物均进行了~1H NMR和^(13)C NMR核磁共振表征。

The catalytic reduction of acyl azides to amides by reaction with hydrosilanes was reported. The various combinations of Cu Cln/NHC·HCl catalyst precursors( n = 1,2; NHC = N-heterocyclic carbenes) and hydrosilanes were examined. The most efficient CuCl/IPr·HCl( IPr = N,N'-bis-( 2,6-diisopropylphenyl) imidazol-2-ylidene) catalytic system by employing(EtO)_3 SiH as the reducing agent had been developed.The starting materials and catalysts were cheap and easy to obtain. Diverse primary amides were obtained in moderate to excellent yields with high functional group tolerance under mild conditions. Therefore,the reported method was novel and efficient for reduction of acyl azides to the corresponding amides.All the products were characterized by ~1 H NMR and ^(13)C NMR spectra.