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Halogen Bond‐Catalyzed Friedel−Crafts Reactions of Furans Using a 2,2’‐Bipyridine‐Based Catalyst
Author(s) -
Zhang Huimiao,
Toy Patrick H.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001019
Subject(s) - chemistry , electrophile , catalysis , friedel–crafts reaction , halogen bond , halogen , acetonitrile , organic chemistry , bipyridine , organocatalysis , polymer chemistry , combinatorial chemistry , alkyl , enantioselective synthesis , crystal structure
A halogen bond donor based on a 2,2’‐bipyridine framework has been synthesized, and used to catalyze Friedel−Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst.