Hexafluoroantimonic Acid Catalysis: Formal [3+2+2] Cycloaddition of Aziridines with Two Alkynes |
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| Authors: | Ming‐Bo Zhou Ren‐Jie Song Prof?Dr Jin‐Heng Li |
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| Institution: | 1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China);2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China) |
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| Abstract: | A practical method for the synthesis of azepine derivatives, a typical seven‐membered heterocyclic ring system, was developed and involves the use of hexafluoroantimonic acid to catalyze a formal 3+2+2] cycloaddition of aziridines with two alkynes. This method was applicable to two of the same or different terminal alkynes for the 3+2+2] cycloaddition with unactivated aziridines, and furnished the corresponding azepine derivatives in good yields with good levels of chemo‐ and regioselectivity. The mechanism was also discussed according to the results of the in situ HRMS and 1H NMR analysis. |
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| Keywords: | alkynes aziridines cycloaddition heterocycles superacidic systems |
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