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Influence of sulfonyl substituents on the decomposition of N-sulfonylhydrazones at room temperature

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Abstract

A detailed study of the dissociation performance of structurally varied N-sulfonylhydrazones was described, and N-tfsylhydrazone was proved to be the best substrate to give the corresponding diazo compound at room temperature. N-Tfsylhydrazone is capable of releasing nonstabilized aryldiazomethane in a wide range of solvents in the presence of various commonly used bases under mild reaction conditions (−25 °C to 40 °C). The utility of the strategy is established by late-stage derivatization of bioactive molecules and several typically sensitive reactions, in which highly purified diazo compounds are required.

Graphical abstract: Influence of sulfonyl substituents on the decomposition of N-sulfonylhydrazones at room temperature

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Publication details

The article was received on 01 Aug 2018, accepted on 27 Nov 2018 and first published on 05 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO00802G
Citation: Org. Chem. Front., 2019, Advance Article
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    Influence of sulfonyl substituents on the decomposition of N-sulfonylhydrazones at room temperature

    Z. Liu, K. Raveendra Babu, F. Wang, Y. Yang and X. Bi, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO00802G

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