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 Leq 2018
Accepted
27 Xim 2018
First published
05 Kax 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements