Hao Wei, Geng Weizhi, Zhang Wen-Xiong, Xi Zhenfeng
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-62751708.
Chemistry. 2014 Feb 24;20(9):2605-12. doi: 10.1002/chem.201304215. Epub 2014 Jan 21.
An efficient synthesis of N-substituted indole derivatives was realized by combining the Pd-catalyzed one-pot multicomponent coupling approach with cleavage of the C(sp(3))-N bonds. Three or four components of aryl iodides, alkynes, and amines were involved in this coupling process. The cyclopentadiene-phosphine ligand showed high efficiency. A variety of aryl iodides, including cyclic and acyclic tertiary amino aryl iodides, and substituted 1-bromo-2-iodobenzene derivatives could be used. Both symmetric and unsymmetric alkynes substituted with alkyl, aryl, or trimethylsilyl groups could be applied. Cyclic secondary amines such as piperidine, morpholine, 4-methylpiperidine, 1-methylpiperazine, 2-methylpiperidine, and acyclic amines including secondary and primary amines all showed good reactivity. Further application of the resulting indole derivatives was demonstrated by the synthesis of benzosilolo[2,3-b]indole.
通过将钯催化的一锅多组分偶联方法与C(sp(3))-N键的裂解相结合，实现了N-取代吲哚衍生物的高效合成。芳基碘化物、炔烃和胺的三种或四种组分参与了该偶联过程。环戊二烯-膦配体显示出高效率。可以使用各种芳基碘化物，包括环状和非环状叔氨基芳基碘化物以及取代的1-溴-2-碘苯衍生物。可以应用被烷基、芳基或三甲基甲硅烷基取代的对称和不对称炔烃。环状仲胺如哌啶、吗啉、4-甲基哌啶、1-甲基哌嗪、2-甲基哌啶以及包括仲胺和伯胺在内的非环状胺都表现出良好的反应性。通过苯并硅并环戊二烯并[2,3-b]吲哚的合成证明了所得吲哚衍生物的进一步应用。
