Ionic liquids/[bmim][N3] mixtures: promising media for the synthesis of aryl azides by SNAr

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Abstract

The nucleophilic aromatic substitution of some activated aryl or heteroaryl halides has been performedin ionic liquid solution, using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction coursewas studied varying the structures of both substrates and ionic liquids. In particular, in the latter case, thereaction of 2-bromo-5-nitrothiophene was carried out in five different ionic liquids ([bmim][BF4],[bmim][PF6], [bmim][NTf2], [bm2im][NTf2], and [bmpyrr][NTf2]). Finally, for all the substrates considered,a comparison with data obtained in MeOH solution in the presence of NaN3 was also performed. Datacollected indicate that in some cases it is possible to obtain aromatic or heteroaromatic azide derivativesin satisfactory yield by means of a SNAr reaction using [bmim][N3] as the nucleophile.
Lingua originaleEnglish
pagine (da-a)6224-6228
Numero di pagine5
RivistaJournal of Organic Chemistry
Volume73
Stato di pubblicazionePublished - 2008

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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