Intramolecular C−H Amination of N-Alkylsulfamides by tert-Butyl Hypoiodite or N-Iodosuccinimide |
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Authors: | Dr Kensuke Kiyokawa Keisuke Jou Prof Dr Satoshi Minakata |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2–1, Suita, Osaka, 565-0871 Japan |
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Abstract: | 1,3-Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C−H amination of N-alkylsulfamide derivatives is a reliable method for the construction of 1,3-diamine structures, the majority of these methods involve the use of a transition-metal catalyst. We herein report on a new transition-metal-free method using tert-butyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS), enabling secondary non-benzylic and tertiary C−H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3-diamines. Mechanistic investigations revealed that amination reactions using t-BuOI or NIS each proceed via different pathways. |
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Keywords: | amination heterocycles iodine radical synthetic methods |
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