Premium
Halogen Bond Catalyzed Bromocarbocyclization
Author(s) -
Chan YukCheung,
Yeung YingYeung
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800261
Subject(s) - chemistry , halogenation , halogen , electrophile , halogen bond , trifluoromethanesulfonate , catalysis , organic chemistry , chemoselectivity , combinatorial chemistry , medicinal chemistry , alkyl
A halogen bond catalyzed bromo‐carbocyclization of N ‐cinnamyl sulfonamides and O ‐cinnamyl phenyl ethers has been developed. N ‐methyl 4‐iodopyridinium triflate is used as the halogen‐bonding organocatalyst and the reaction is highly chemoselective. This report represents the first proof‐of‐concept for halogen‐bonding organocatalyst‐promoted electrophilic halogenation. Mechanistic study suggests the autocatalytic nature of this reaction.