Electroreductive nucleophile acceptor generation. Electrochemical synthesis of N-(4-(dimethylamino)phenyl)benzenesulfonamide

Sadegh Khazalpour, Davood Nematollahi, Azizan Ahmad, Bahram Dowlati

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

To the best of our knowledge, this is first report describing generation of Michael acceptor via electrochemical reduction. In this work, electrochemical reduction of 4-nitroso-N,N-dimethylaniline has been studied in the presence of arylsulfinic acids in aqueous solutions. The cathodically generated p-quinonediimine participates in Michael type addition reaction with arylsulfinic acids and converts to the corresponding sulfonamide derivatives. This work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some sulfonamide derivatives with safe waste under green conditions.

Original languageEnglish
Pages (from-to)909-913
Number of pages5
JournalElectrochimica Acta
Volume180
DOIs
Publication statusPublished - 20 Oct 2015

Fingerprint

Nucleophiles
Sulfonamides
Derivatives
Addition reactions
Acids
benzenesulfonamide
N,N-dimethylaniline

Keywords

  • 4-Nitroso-N N-dimethylaniline
  • Cyclic voltammetry
  • Electrochemical synthesis
  • Michael type reaction
  • Sulfonamide

ASJC Scopus subject areas

  • Electrochemistry
  • Chemical Engineering(all)

Cite this

Electroreductive nucleophile acceptor generation. Electrochemical synthesis of N-(4-(dimethylamino)phenyl)benzenesulfonamide. / Khazalpour, Sadegh; Nematollahi, Davood; Ahmad, Azizan; Dowlati, Bahram.

In: Electrochimica Acta, Vol. 180, 20.10.2015, p. 909-913.

Research output: Contribution to journalArticle

@article{ccf933a20f8d467594930a7dff747701,
title = "Electroreductive nucleophile acceptor generation. Electrochemical synthesis of N-(4-(dimethylamino)phenyl)benzenesulfonamide",
abstract = "To the best of our knowledge, this is first report describing generation of Michael acceptor via electrochemical reduction. In this work, electrochemical reduction of 4-nitroso-N,N-dimethylaniline has been studied in the presence of arylsulfinic acids in aqueous solutions. The cathodically generated p-quinonediimine participates in Michael type addition reaction with arylsulfinic acids and converts to the corresponding sulfonamide derivatives. This work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some sulfonamide derivatives with safe waste under green conditions.",
keywords = "4-Nitroso-N N-dimethylaniline, Cyclic voltammetry, Electrochemical synthesis, Michael type reaction, Sulfonamide",
author = "Sadegh Khazalpour and Davood Nematollahi and Azizan Ahmad and Bahram Dowlati",
year = "2015",
month = "10",
day = "20",
doi = "10.1016/j.electacta.2015.09.031",
language = "English",
volume = "180",
pages = "909--913",
journal = "Electrochimica Acta",
issn = "0013-4686",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Electroreductive nucleophile acceptor generation. Electrochemical synthesis of N-(4-(dimethylamino)phenyl)benzenesulfonamide

AU - Khazalpour, Sadegh

AU - Nematollahi, Davood

AU - Ahmad, Azizan

AU - Dowlati, Bahram

PY - 2015/10/20

Y1 - 2015/10/20

N2 - To the best of our knowledge, this is first report describing generation of Michael acceptor via electrochemical reduction. In this work, electrochemical reduction of 4-nitroso-N,N-dimethylaniline has been studied in the presence of arylsulfinic acids in aqueous solutions. The cathodically generated p-quinonediimine participates in Michael type addition reaction with arylsulfinic acids and converts to the corresponding sulfonamide derivatives. This work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some sulfonamide derivatives with safe waste under green conditions.

AB - To the best of our knowledge, this is first report describing generation of Michael acceptor via electrochemical reduction. In this work, electrochemical reduction of 4-nitroso-N,N-dimethylaniline has been studied in the presence of arylsulfinic acids in aqueous solutions. The cathodically generated p-quinonediimine participates in Michael type addition reaction with arylsulfinic acids and converts to the corresponding sulfonamide derivatives. This work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some sulfonamide derivatives with safe waste under green conditions.

KW - 4-Nitroso-N N-dimethylaniline

KW - Cyclic voltammetry

KW - Electrochemical synthesis

KW - Michael type reaction

KW - Sulfonamide

UR - http://www.scopus.com/inward/record.url?scp=84941883608&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84941883608&partnerID=8YFLogxK

U2 - 10.1016/j.electacta.2015.09.031

DO - 10.1016/j.electacta.2015.09.031

M3 - Article

AN - SCOPUS:84941883608

VL - 180

SP - 909

EP - 913

JO - Electrochimica Acta

JF - Electrochimica Acta

SN - 0013-4686

ER -