Iodine-Catalyzed Diazenylation with Arylhydrazine Hydrochlorides in Air

The Journal of Organic Chemistry
Dinesh S BarakSanjay Batra

Abstract

A mild approach to diazenylation of active methylene compounds and N-heterocyclic compounds with arylhydrazine hydrochlorides in the presence of iodine under basic aerobic conditions was developed. The reaction could be executed either under heating or in the presence of blue LED light, though the latter condition was found to be relatively efficient. Presumably, the aryldiazene produced by oxidation of arylhydrazine hydrochloride acts as a nitrogen scavenger of the radical intermediate generated from the active methylene compound in the presence of iodine to produce the diazo compounds. The scope and limitations of the protocol are presented.

References

Feb 10, 1976·Biochemistry·H P Misra, I Fridovich
Nov 14, 2002·Chemical Reviews·Almeria Natansohn, Paul Rochon
Sep 12, 2003·Nature·Yanlei YuTomiki Ikeda
Jan 16, 2007·The Journal of Organic Chemistry·Markus R HeinrichAlexander Wetzel
Sep 21, 2007·Expert Opinion on Drug Delivery·Marta RoldoJohn Tsibouklis
Oct 26, 2007·Journal of the American Chemical Society·Eyal Drug, Michael Gozin
Dec 17, 2008·Science·Abdessamad GrirraneHermenegildo García
Mar 17, 2011·Chemical Society Reviews·Estíbaliz Merino
Apr 13, 2011·Chemical Society Reviews·Andrew A Beharry, G Andrew Woolley
Oct 27, 2011·The Journal of Organic Chemistry·David A KennedyMarc Devocelle
Nov 24, 2011·Angewandte Chemie·Timm FehrentzDirk Trauner
Nov 8, 2012·The Journal of Organic Chemistry·Hannelore JaschMarkus R Heinrich
Apr 26, 2013·Chemical Reviews·Wiktor SzymańskiBen L Feringa
Jan 17, 2014·Chemical Society Reviews·Xin Su, Ivan Aprahamian
Feb 15, 2014·The Journal of Organic Chemistry·Josefa HofmannMarkus R Heinrich
Apr 16, 2014·The Journal of Organic Chemistry·Bo JiangGuigen Li
Aug 27, 2014·Angewandte Chemie·Stefanie K FehlerMarkus R Heinrich
Apr 22, 2015·The Journal of Organic Chemistry·Makthala RaviPrem P Yadav
Sep 29, 2015·Accounts of Chemical Research·Mingxin DongG Andrew Woolley

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Citations

Feb 6, 2020·The Journal of Organic Chemistry·Saibal SarSubhabrata Sen

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