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

以3,5-二三氟甲基苯胺、乙二醛、甲醛、氯化铵和氯化苄或1-溴癸烷为原料,经缩合、亲核取代反应得到氯化1-苄基-3-(3,5-二三氟甲基)苯基咪唑盐和溴化1-癸基-3-(3,5-二三氟甲基)苯基咪唑盐,收率分别达59.0%和76.6%;通过氯化1-苄基-3-(3,5-二三氟甲基)苯基咪唑盐和溴化1-癸基-3-(3,5-二三氟甲基)苯基咪唑盐的阴离子交换反应得到4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、1-癸基-3-(3,5-二三氟甲基)苯基咪唑四氟硼酸盐、1-苄基-3-(3,5-二三氟甲基)苯基咪唑六氟磷酸盐和1-癸基-3-(3,5-二三氟甲基)苯基咪唑六氟磷酸盐,产物结构通过1HNMR、13CNMR得以确认。考察了溶剂对亲核取代反应的影响,得出最佳反应溶剂为甲苯。

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 76.6% respectively. The compounds of 1-benzyl-3-[ 3, 5-bis （ trifluoromethyl ）] phenyl imidazole tetrafluoroborate, 1 -decyl-3- [ 3,5-bis （ trifluoromethyl ） ] phenyl imidazole tetrafluoroborate, 1 -benzyl-3- [ 3, 5-bis （trifluoromethyl）] phenyl imidazole hexafluorophosphate and 1-decyl-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 and bromide 1-decyl-3-[ 3, 5-bis （trifluoromethyl）J phenyl imidazote salt. All the compounds were characterized by means of 1HNMR and 13CNMR. The effect of solvent on the nucleophilic substitution reaction was studied. The results indicate that toluene is the optimal reaction solvent.