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Aryldiazonium ion initiated C–N bond cleavage for the versatile, efficient and regioselective ring opening of aziridines

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Abstract

Aryldiazonium salts have been proved to initiate the regioselective cleavage of aziridines for the installation of varied functional groups. The ring-opening process is effective and general for a variety of nucleophiles, including [O], [S] and [N], at room temperature. This highly regioselective process, which can be performed at the gram scale, enjoys operational simplicity, as well as mild and metal-free conditions. The postulated reaction mechanism involves a single electron transfer from aziridines to aryldiazonium salts, which generates a highly reactive amino radical cation.

Graphical abstract: Aryldiazonium ion initiated C–N bond cleavage for the versatile, efficient and regioselective ring opening of aziridines

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Publication details

The article was received on 01 Mar 2019, accepted on 03 Apr 2019 and first published on 04 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00320G
Org. Chem. Front., 2019, Advance Article

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    Aryldiazonium ion initiated C–N bond cleavage for the versatile, efficient and regioselective ring opening of aziridines

    X. Zhang, X. Qiu, J. Rong, Z. Su, X. Cui and C. Tao, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00320G

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