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Synthesis of Eight‐Membered Nitrogen Heterocycles via a Heterogeneous PtI 2 ‐Catalyzed Cascade Cycloaddition Reaction of δ‐Aminoalkynes with Electron‐Deficient Alkynes
Author(s) -
Li Xinhong,
Wang Songmeng,
Wang Hongkai,
Wang Weilin,
Liu Lingyan,
Chang Weixing,
Li Jing
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901644
Subject(s) - chemistry , cycloaddition , intramolecular force , cascade reaction , catalysis , cascade , intermolecular force , combinatorial chemistry , ring (chemistry) , reaction conditions , nitrogen , organic chemistry , computational chemistry , photochemistry , molecule , chromatography
A novel heterogeneous PtI 2 ‐catalyzed cascade reaction of δ‐aminoalkynes was developed for the synthesis of various eight‐membered nitrogen heterocycles in excellent yields. The reaction proceeds via a hydration of δ‐aminoalkynes and subsequent intramolecular cyclization and intermolecular addition as well as ring‐expansion cascade reaction with another electron‐deficient alkynes. This method has the advantages of simple operation and mild reaction conditions. And the simple PtI 2 with no any supports could be readily recycled through simple centrifugation without substantial loss of activity in 1,2‐dichloroethane (DCE). The recyclability of PtI 2 may be ascribed to its insolubility in DCE. The reaction constitutes a formal [6+2]‐cycloaddition.