Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
19 ذو القعدة 1439
Accepted
19 ربيع الأول 1440
First published
27 ربيع الأول 1440

Org. Chem. Front., 2019,6, 121-124

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, 6, 121 DOI: 10.1039/C8QO00802G

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