Construction of multiple bondsviaa domino reaction of trifluoroacetimidoyl nitriles within situgenerated bis-nucleophiles
Construction of multiple bondsviaa domino reaction of trifluoroacetimidoyl nitriles within situgenerated bis-nucleophiles
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通过原位双亲核试剂内三氟乙酰亚氨基腈的多米诺骨牌反应构建多重键
DOI：
10.1039/d0cc02398a
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发表时间：
2020
影响因子：
4.9
通讯作者：
Liu Pei-Nian
中科院分区：
文献类型：
--
作者：
Li Deng-Yuan;Chen Jia-Yan;Feng Da-Fu;Chen Shuang;Xu Xian-Kuan;Dang Li;Liu Pei-Nian
发展了一种不含过渡金属的双加成/双重排多米诺反应，得到了CF 3取代的嘧啶类化合物，该反应一锅法合成了5个新键，即3个C-C键和2个C-N键.实现这种高效反应的关键包括精细设计的双亲核试剂原位生成的二聚的烷基腈和使用的三氟乙酰亚胺基腈含有CN，CN和CF 3基团作为反应物。通过实验和密度泛函理论计算对反应机理进行了研究，发现该反应涉及两个加成和两个重排过程。
A transition-metal-free double addition/double rearrangement domino reaction affording CF3-substituted pyrimidines was developed, which enables the one-pot construction of five new bonds, namely three C–C bonds and two C–N bonds. The keys to achieve this highly efficient reaction include the delicate design of the bis-nucleophiles in situ generated from the dimerization of alkyl nitriles and the use of trifluoroacetimidoyl nitriles containing CN, CN, and CF3 groups as the reactant. The mechanistic studies by the experiments and DFT calculations reveal that the transformation involves two addition and two unprecedented rearrangement processes.