Diiodomethane-Mediated Generation of N-Aryliminium Ions and Subsequent [4 + 2] Cycloadditions with Olefins.,The Journal of Organic Chemistry

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Diiodomethane-Mediated Generation of N-Aryliminium Ions and Subsequent [4 + 2] Cycloadditions with Olefins.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-09 , DOI: 10.1021/acs.joc.9b03148
Yu-Quan Zhao ₁ , Jun-Jie Tian ₁ , Chong-Ren Ai ₁ , Xiao-Chen Wang ₁

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Herein, we report a method for in situ generation of N-aryliminium ions via reactions of N,N-dimethylanilines with diiodomethane. We used the method to prepare tetrahydroquinolines via one-pot three-component reactions between N,N-dimethylanilines, diiodomethane, and olefins. This transformation involves initial reaction of the aniline with diiodomethane to form an iodomethylammonium salt, which undergoes fragmentation accompanied by elimination of methyl iodide to give an N-aryliminium ion, which is trapped by the olefin via [4 + 2] cycloaddition to give the final product. This method for generating N-aryliminium ions requires neither a catalyst nor a strong oxidant, suggesting that it can be expected to find broad utility, especially for substrates that are sensitive to Lewis acids, transition metals, or strong oxidants.

中文翻译：

二碘甲烷介导的N-芳基亚胺离子的生成以及随后的[4 + 2]与烯烃的环加成反应。

在此，我们报告了一种通过N，N-二甲基苯胺与二碘甲烷反应原位生成N-芳基亚胺离子的方法。我们使用该方法通过N，N-二甲基苯胺，二碘甲烷和烯烃之间的一锅三组分反应制备四氢喹啉。此转化过程涉及苯胺与二碘甲烷的初始反应，形成碘甲基铵盐，然后进行裂解并消除甲基碘，得到N-芳基亚胺离子，该烯烃经[4 + 2]环加成反应被烯烃捕获，得到最终产物。产品。这种产生N-芳基亚胺离子的方法既不需要催化剂也不需要强氧化剂，这表明可以预期它具有广泛的用途，特别是对于对路易斯酸，过渡金属或强氧化剂敏感的底物。

更新日期：2020-01-23

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