Jump to main content
Jump to site search

Issue 29, 2018
Previous Article Next Article

Metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones

Author affiliations

Abstract

A novel, metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones via a [3 + 2] cycloaddition reaction using sulfonyl azides under mild reaction conditions is reported. In this straightforward atom- and step-economical protocol, the active alkene moiety of quinone undergoes a thermal azide–alkene [3 + 2] cycloaddition followed by proton abstraction, ring opening and elimination of a nitrogen molecule to form sulfonamidation products in good yield and all the synthesized sulfonamidation derivatives exhibit good absorption and emission characteristics. In addition, the electrochemical properties of both 1,4-naphthoquinone and menadione sulfonamidation derivatives are studied and significant redox potentials are observed. Other important features of this methodology are readily accessible and easy to handle starting materials, milder conditions, reaction with a wide range of substrates and shorter reaction times with good yields.

Graphical abstract: Metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones

Back to tab navigation

Supplementary files

Article information


Submitted
06 Apr 2018
Accepted
27 Jun 2018
First published
30 Jun 2018

Org. Biomol. Chem., 2018,16, 5294-5300
Article type
Paper

Metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones

R. Devenderan and P. Kasi, Org. Biomol. Chem., 2018, 16, 5294
DOI: 10.1039/C8OB00818C

Social activity

Search articles by author

Spotlight

Advertisements