The Smallest Monofluorodiazoethane Reagent and Its[3+2]Cycloaddition Reactions  

作　　者：Xiaodong Tang Ming-Yue He Ran Guo Hao-Nan Liu Jing Nie Ilan Marek Jun-An Ma Fa-Guang Zhang 

机构地区：[1]Department of Chemistry,Tianjin Key Laboratory of Molecular Optoelectronic Sciences,Frontiers Science Center for Synthetic Biology(Ministry of Education),Tianjin University,Tianjin 300072 [2]Joint School of National University of Singapore and Tianjin University,International Campus of Tianjin University,Binhai New City,Fuzhou 350207 [3]Department of Medicinal Chemistry,School of Pharmacy,Hebei Medical University,Shijiazhuang 050017 [4]Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis,Technion–Israel Institute of Technology,Haifa 3200009

出　　处：《CCS Chemistry》2024年第11期2825-2834,共10页中国化学会会刊（英文）

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).

摘　　要：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.

关 键 词：monofluoromethyl group diazo reagent cycloaddition reaction TETRAZOLE ISOXAZOLE fluorine chemistry 

分 类 号：O62[理学—有机化学]