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Synthesis of 1‐Vinyl/Arylbenzotriazole 3‐Oxides through a Copper‐Mediated C–N Bond Coupling Reaction
Author(s) -
Shi WeiMin,
Liu FengPing,
Wang ZhiXin,
Bi HongYan,
Liang Cui,
Xu LiPing,
Su GuiFa,
Mo DongLiang
Publication year - 2017
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.201700462
Subject(s) - chemistry , benzotriazole , functional group , copper , substrate (aquarium) , density functional theory , coupling reaction , molecule , oxide , coupling (piping) , combinatorial chemistry , polymer chemistry , organic chemistry , computational chemistry , catalysis , mechanical engineering , oceanography , engineering , geology , polymer
An efficient synthesis of 1‐vinyl/arylbenzotriazole 3‐oxides via the copper‐promoted coupling of N ‐hydroxybenzotriazoles with alkenyl‐ or arylboronic acids is reported. This strategy features mild reaction conditions, good functional group tolerance, broad substrate scope and rapid introduction of benzotriazole N ‐oxide moieties into molecules. Density functional theory calculations revealed that the formation of the favored N ‐coupling product depends on the kinetically more favorable C–N bond formation pathway.