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A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

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Abstract

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

Graphical abstract: A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

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Publication details

The article was received on 11 Jul 2019, accepted on 29 Jul 2019 and first published on 29 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01547G
Org. Biomol. Chem., 2019, Advance Article

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    A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

    G. Zhang, Y. Zhao and C. Ding, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01547G

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