Accessing Azetidines through Magnesium-Mediated Nitrogen Group Transfer from Iminoiodinane to Donor-Acceptor Cyclopropanes.

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Tác giả: Mahmoud Afrasi, Ajay H Bansode, Ning Deng, Marvin Parasram, Lifeng Yin, Yiyi Zhu

Ngôn ngữ: eng

Ký hiệu phân loại: 303 Social processes

Thông tin xuất bản: Germany : Angewandte Chemie (International ed. in English) , 2025

Mô tả vật lý:

Bộ sưu tập: NCBI

ID: 176511

Herein, we report a Lewis acid-mediated ring expansion of donor-acceptor cyclopropanes (DACs) to substituted azetidines via nucleophilic nitrogen group transfer from readily accessible iminoiodinane. This protocol operates under mild, transition-metal-free conditions, and showcases excellent chemoselectivity, along with broad functional group tolerance. We report for the first time that challenging alkyl donor-acceptor cyclopropanes can undergo ring expansion leading to aliphatic azetidines without relying on external oxidants or precious transition-metal catalysts. Mechanistically, the coordination of a magnesium (Mg)-Lewis acid to the DAC promotes nucleophilic ring opening with a putative Mg-amide species generated from the iminoiodinane under the reaction conditions to furnish the azetidine products.
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