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
01 Aug. 2018
Accepted
27 Nov. 2018
First published
05 Dec. 2018

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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