Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles

A familiar ring? Highly N2‐selective arylation of 4,5‐unsubstituted and 4‐substituted 1,2,3‐triazoles was achieved for the first time by the Pd/1 catalyst system. A wide range of N2‐aryl‐1,2,3‐triazoles were prepared from aryl bromides, chlorides, and triflates with excellent N2 selectivity (see sch...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 38; pp. 8944 - 8947
Main Authors Ueda, Satoshi, Su, Mingjuan, Buchwald, Stephen L.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.09.2011
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Catalysis
CN coupling
heterocycles
homogeneous catalysis
N-arylation
Nitrogen - chemistry
palladium
Palladium - chemistry
Triazoles - chemistry
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Summary:A familiar ring? Highly N2‐selective arylation of 4,5‐unsubstituted and 4‐substituted 1,2,3‐triazoles was achieved for the first time by the Pd/1 catalyst system. A wide range of N2‐aryl‐1,2,3‐triazoles were prepared from aryl bromides, chlorides, and triflates with excellent N2 selectivity (see scheme). Density functional theory calculations suggest that the formation of N2‐arylated 1,2,3‐triazoles is favored kinetically. dba=dibenzylideneacetone, Tf=trifluoromethanesulfonyl.
Bibliography:istex:B1D619853DDDCB0DCF13CE6BDE56673ED4F6BE6B
This work is supported by the National Institutes of Health (GM58160). S.U. thanks the Japan Society for the Promotion of Sciences (JSPS) for a Postdoctral Fellowship for Research Abroad. We thank Dr. Thomas J. Maimone for help with preparation of this manuscript.
ark:/67375/WNG-VWJ4HPTH-L
JSPS
ArticleID:ANIE201103882
National Institutes of Health - No. GM58160
Japan Society for the Promotion of Science
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103882