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Ionic Liquids/[bmim][N3] Mixtures: Promising Media for the Synthesis of Aryl Azides by SNAr.

  作者 D'Anna, Francesca;Marullo, Salvatore;Noto, Renato;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-16;  页码  6224-6228  
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[摘要]The nucleophilic arom. substitution of some activated aryl or heteroaryl halides has been performed in ionic liq. soln., using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction course was studied varying the structures of both substrates and ionic liqs. In particular, in the latter case, the reaction of 2-bromo-5-nitrothiophene was carried out in five different ionic liqs. ([bmim][BF4], [bmim][PF6], [bmim][NTf2], [bm2im][NTf2], and [bmpyrr][NTf2]). Finally, for all the substrates considered, a comparison with data obtained in MeOH soln. in the presence of NaN3 was also performed. Data collected indicate that in some cases it is possible to obtain arom. or heteroarom. azide derivs. in satisfactory yield by means of a SNAr reaction using [bmim][N3] as the nucleophile.

 
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