Ionic liquids/[bmim][N3] mixtures: promising media for the synthesis of aryl azides by SNAr |
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Authors: | D'Anna Francesca Marullo Salvatore Noto Renato |
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Institution: | Dipartimento di Chimica Organica E. Paternò, Università degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans II, 90128 Palermo, Italy. fdanna@unipa.it |
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Abstract: | The nucleophilic aromatic substitution of some activated aryl or heteroaryl halides has been performed in ionic liquid solution, using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction course was studied varying the structures of both substrates and ionic liquids. In particular, in the latter case, the reaction of 2-bromo-5-nitrothiophene was carried out in five different ionic liquids (bmim]BF 4], bmim]PF 6], bmim]NTf 2], bm 2im]NTf 2], and bmpyrr]NTf 2]). Finally, for all the substrates considered, a comparison with data obtained in MeOH solution in the presence of NaN 3 was also performed. Data collected indicate that in some cases it is possible to obtain aromatic or heteroaromatic azide derivatives in satisfactory yield by means of a S NAr reaction using bmim]N 3] as the nucleophile. |
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