The first example of direct cyclopropylation of arylamines at the 2-position with magnesium cyclopropylidenes |
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| Authors: | Yukie Yamada |
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| Institution: | Department of Chemistry, Faculty of Science, Tokyo University of Science, Ichigaya-funagawara-machi 12, Shinjuku-ku, Tokyo 162-0826, Japan |
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| Abstract: | Treatment of magnesium cyclopropylidenes, which were generated from 1-chlorocyclopropyl phenyl sulfoxides with isopropylmagnesium chloride in THF at −78 °C, with N-lithio arylamines gave arylamines cyclopropylated at the 2-position in moderate to good yields. Use of the magnesium cyclopropylidenes having at least one substituent was found to be essential to this cyclopropylation. This procedure offers a novel synthesis of arylamines having a cyclopropane ring at the 2-position directly from arylamines. |
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| Keywords: | Magnesium cyclopropylidene Magnesium carbenoid Sulfoxide-magnesium exchange reaction Cyclopropylation 2-Cyclopropylated arylamine |
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