Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 16, Pages 2741-2746Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700462
Keywords
benzotriazole oxides; C-N bond formation; copper catalysis; N-O compounds; organoboronic acids
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Funding
- National Natural Science Foundation of China [21562005, 21602037, 21462008]
- Natural Science Foundation of Guangxi [2016GXNSFFA380005]
- Overseas 100 Talents Program of Guangxi Higher Education
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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.
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