一种新型3-芳基咪唑卡宾前体的合成

Synthesis of a new type of 3-aryl imidazolium N-Heterocyclic Carbene Predecessor

摘要:

以3,5-二三氟甲基苯胺、乙二醛、甲醛、氯化铵和氯化苄或1-溴葵烷为原料，经缩合、亲核取代得到氯化1-苄基-3-(3,5-二三氟甲基)苯基咪唑盐和溴化1-葵基-3-(3, 5-二三氟甲基)苯基咪唑盐，收率分别达59.0%和77.1%；通过氯化1-苄基-3-(3,5-二三氟甲基)苯基咪唑盐的阴离子交换反应得到2种目标产物：1-苄基-3-(3,5-二三氟甲基)苯基咪唑四氟硼酸盐和1-苄基-3-(3,5-二三氟甲基)苯基咪唑六氟磷酸盐，产物结构通过1H NMR，13C NMR得以确认。考察了溶剂对亲核取代反应的影响，实验结果表明，当以甲苯为反应溶剂时，效果最好，收率达59.0%。

Abstract:

Chloride 1-benzyl-3-(3,5-bis (trifluoromethyl)) phenyl imidazole salt and bromide 1- decyl-3-(3,5-bis (trifluoromethyl)) phenyl imidazole salt were synthesized from 3,5-bis (trifluoromethyl) aniline, formaldehyde, glyoxal, ammonium chloride and benzyl chloride or 1-bromodecane by condensation reaction, nucleophilic substitution reaction and the yields were 59.0% and 77.1%. The compounds of 1-benzyl-3-(3,5-bis (trifluoromethyl)) phenyl imidazole tetrafluoroborate and 1-benzyl-3-(3,5-bis (trifluoromethyl)) phenyl imidazole hexafluorophosphate were designed and synthesized by anion exchange reaction of chloride 1-benzyl-3-(3,5-bis ( trifluoromethyl)) phenyl imidazole salt. All the compounds were characterized by means of 1H NMR and 13C NMR. The effect of solvent on the nucleophilic substitution reaction was studied. The results demonstrated that toluene as solvent, the yield was 59.0%.