An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation

M. Sheykhan; S. Khani; M. Abbasnia; S. Shaabanzadeh; M. Joafshan

doi:10.1039/C7GC03141F

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An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation†‡

M. Sheykhan,

*^a S. Khani,^a M. Abbasnia,*^bc S. Shaabanzadeh^a and M. Joafshan^a

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* Corresponding authors

^a Chemistry Department, University of Guilan, P.O. Box 41335-1914, Rasht, Iran
E-mail: sheykhan@guilan.ac.ir
Fax: +981333367262

^b School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran

^c School of Pharmacy, Guilan University of Medical Sciences, Rasht, Iran

Abstract

tert-Amines were harnessed to afford arenesulfonyl hydrazides and arenesulfonyl chlorides via a metal-, oxidant- and halogen-free electrochemical oxidative coupling in an undivided cell at RT. This environmentally benign approach afforded a wide spectrum of sulfonamides in satisfactory yields using cheap and renewable Pencil Graphite Electrodes (PGEs).

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Article information

DOI: https://doi.org/10.1039/C7GC03141F
Article type: Paper
Submitted: 19 Oct 2017
Accepted: 14 Nov 2017
First published: 17 Nov 2017

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Green Chem., 2017,19, 5940-5948

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An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation

M. Sheykhan, S. Khani, M. Abbasnia, S. Shaabanzadeh and M. Joafshan, Green Chem., 2017, 19, 5940 DOI: 10.1039/C7GC03141F

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Green Chemistry

An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation†‡

Abstract

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An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation

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