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Hypervalent Iodine‐Mediated and Traceless Fluorine‐Oriented: Synthesis of 5‐Methyl‐1,2,3,4‐tetrahydropyridine from Unactivated Alkenes
Author(s) -
Zhang LuWen,
Huang Xie,
Wang JiaQi,
He Wei
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100290
Subject(s) - hypervalent molecule , chemistry , trifluoromethylation , intramolecular force , reagent , fluorine , iodine , fluoride , combinatorial chemistry , organic chemistry , trifluoromethyl , inorganic chemistry , alkyl
An original metal‐free method for the convenient preparation of 5‐methyl‐1,2,3,4‐tetrahydropyridine derivatives from simple unactivated alkenes was firstly developed with excellent yields under mild conditions, based on hypervalent iodine compounds in combination with boron fluoride reagents. Mechanism studies have shown that fluorine participates in the reaction as a traceless guiding group, ensuring the successful construction of the Csp 2 −N bond of tetrahydropyridine derivatives via the selective intramolecular coupling reaction of unactivated alkenes.