Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: multicomponent synthesis of glutarimides.
Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: multicomponent synthesis of glutarimides.
复制标题
DOI：
10.1002/anie.200351689
复制
发表时间：
2003-07
影响因子：
--
通讯作者：
H. Takaya;Kazunori Yoshida;Katsuhiro Isozaki;Hiroki Terai;S. Murahashi
中科院分区：
文献类型：
--
作者：
H. Takaya;Kazunori Yoshida;Katsuhiro Isozaki;Hiroki Terai;S. Murahashi
刘易斯酸或碱促进的大多数反应都是化学计量反应。基于过渡金属而不是传统的Lewis酸和碱的催化剂可能是有用的，因为不需要中和试剂，也不会形成盐。我们发现这种具有低氧化还原电势的过渡金属路易斯酸[1-4]和碱[1，5]催化剂对环境友好，对有机合成是有用的。这一概念可以扩展到基于过渡金属的亲两亲性催化剂。[6]这些催化剂使得酸和碱促进的反应在一个容器中都可能发生，而不会由于中和而相互破坏试剂，并且可以构建可能用于组合化学的多组分催化反应。我们在这里报道了基于过渡金属的Ir多氢化合物[IrH5(PiPr3)2]1是一种很好的Lewis酸碱双亲催化剂，并且在催化剂1的存在下，腈、烯烃和水发生了一种新的三组分反应得到戊二亚胺，这是合成生物活性化合物[Eq]的高度通用的中间体。1]、[7]Ir络合物1很重要，因为两者
The majority of reactions promoted by Lewis acids or bases are stoichiometric. Catalysts based on transition metals instead of conventional Lewis acids and bases might be useful, because the neutralization of reagents would not be necessary, and salts would not form. We found that such transition-metal-based Lewis acid [1–4] and base [1, 5] catalysts that have low redox potentials are environmentally benign and useful for organic synthesis. This concept can be extended to ambiphilic catalysts based on transition metals.[6] These catalysts make possible both acid-and base-promoted reactions in a single container without the mutual destruction of reagents by neutralization, and multicomponent catalytic reactions that may be useful for combinatorial chemistry can be constructed.We report herein that the iridium polyhydride complex [IrH5 (PiPr3) 2] 1 is an excellent Lewis acid and base ambiphilic catalyst based on a transition metal, and that a novel threecomponent reaction of nitriles, olefins, and water occurs in the presence of catalyst 1 to gave glutarimides, which are highly versatile intermediates for synthesis of biologically active compounds [Eq. 1].[7] Iridium complex 1 is important as both