Given the widespread applications of fluorinated substances in pharmaceuticals,biology,and materials,the development of fluorine-containing building blocks remains an important topic in organic chemistry.In the repert...Given the widespread applications of fluorinated substances in pharmaceuticals,biology,and materials,the development of fluorine-containing building blocks remains an important topic in organic chemistry.In the repertoire of fluorinated diazo compounds,research on tri-and difluorodiazoethane is well-established,but the lack of synthetic methods has left studies related to monofluorodiazoethane as an unexplored territory.In our current work,the taming of the smallest monofluorodiazoethane reagent was realized using two phenylsulfonyl mask groups.This newly synthesized diazo reagent displayed intriguing reactivity patterns:the reaction with aryldiazonium salts gave monofluoromethyl tetrazoles,whereas its reactivity with alkynes and alkenes furnished monofluoromethyl isoxazoles and dihydro-isoxazoles.Furthermore,the removal of the masking groups provided access to a wide range of monofluoromethyl-functionalized heterocycles.展开更多
基金financial support provided by the National Natural Science Foundation of China(NSFC,grant nos.92156025 and 22271212)the National Key Research and Development Program of China(grant nos.2019YFA0905100 and 2021YFF0701700)X.T.thanks the China Postdoctoral Science Foundation(grant no.2022M712350).
文摘Given the widespread applications of fluorinated substances in pharmaceuticals,biology,and materials,the development of fluorine-containing building blocks remains an important topic in organic chemistry.In the repertoire of fluorinated diazo compounds,research on tri-and difluorodiazoethane is well-established,but the lack of synthetic methods has left studies related to monofluorodiazoethane as an unexplored territory.In our current work,the taming of the smallest monofluorodiazoethane reagent was realized using two phenylsulfonyl mask groups.This newly synthesized diazo reagent displayed intriguing reactivity patterns:the reaction with aryldiazonium salts gave monofluoromethyl tetrazoles,whereas its reactivity with alkynes and alkenes furnished monofluoromethyl isoxazoles and dihydro-isoxazoles.Furthermore,the removal of the masking groups provided access to a wide range of monofluoromethyl-functionalized heterocycles.
