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Preparation of Perfluoroalkyl Azaarenes with a Perfluoroalkyllithium-Boron Trifluoride System
In the presence of Borontrifluoride, perfluoroalkyllithiums generated in situ from the reaction of n-perfluoroalkyl iodides with methyllithium-lithium bromide smoothly added to a carbon-nitrogen double bond of bicyclic azaarenes and diazines to give the corresponding perfluoroalkylated dihydro heterocycles, which often underwent spontaneous aromatization in air.Perfluoroalkylation occured preferentially at the carbon next to nitrogen in azaarenes even when the carbon atom was occupied by an alkyl substituent.Only one exception observed was the reaction of acridine where a perfluoroalkyl group was introduced at 9 position.
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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N455 – PubChem