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Transition‐Metal‐free C5, C7‐Dihalogenation and the Switchable C5 Halogenation of 8‐Hydroxyquinolines
Author(s) -
Xiong Jin,
Liu Yunyun
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803965
Subject(s) - halogenation , chemistry , hydrolysis , transition metal , catalysis , electrophile , toluene , combinatorial chemistry , organic chemistry
The first example on the C5, C7‐dihalogenation of 8‐hydroxyquinolines based on an in situ O ‐acyl 8‐hydroxyquinoline formation is realized under catalyst‐free condition in toluene. Modifying the reaction conditions by directly utilizing O ‐acylated 8‐hydroxyquinolines in the presence of AlCl 3 enables the electrophilic halogenation in the C5 position, leading to the tunable synthesis of C5 halogenated products. The O ‐acyl group can be easily removed from the product to provide halogenated quinolines containing free hydroxyl group by simple hydrolysis.