Halogenated 1,2,3-triazole carbene, and preparation method and application thereof
A technology of triazole carbene and triazole carbene, applied in the field of organic catalysis, can solve problems such as limiting the development of triazole carbene
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Embodiment 1
[0101] Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-triazolecarbene
[0102] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-triazole salt
[0103] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30ml of dichloromethane, 1mL (mmol) of 1,1-dichloroethylene and 1.7mL (15mmol) of tert-butyl hypohalite were added in the dark. Allow to warm to room temperature freely. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-chloro-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-tr...
Embodiment 2
[0109] Preparation of 1,3-bis(2,6-diisopropyl-phenyl)-5-bromo-1,2,3-triazolecarbene
[0110] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-bromo-1,2,3-triazole salt
[0111] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30 mL of dichloromethane, 0.8 mL (10 mmol) of 1,2-dibromoethylene and 1.7 mL (15 mmol) of tert-butyl hypohalite were added in the dark. Let it warm up to room temperature naturally. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-bromo-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-bromo-1...
Embodiment 3
[0119] Preparation of 1,3-bis(2,6-diisopropyl-phenyl)-5-fluoro-1,2,3-triazolecarbene
[0120] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-fluoro-1,2,3-triazole salt
[0121] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30 mL of dichloromethane, 0.8 mL (10 mmol) of 1,2-difluoroethylene and 1.7 mL (15 mmol) of tert-butyl hypohalite were added in the dark. Let it warm up to room temperature naturally. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-fluoro-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-flu...
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