Iron-Catalyzed C−O Bond Activation for the Synthesis of Propargyl-1,2,3-triazoles and 1,1-Bis-triazoles

The FeCl3-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and...

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Published inOrganic letters Vol. 12; no. 15; pp. 3308 - 3311
Main Authors Yan, Wuming, Wang, Qiaoyi, Chen, Yunfeng, Petersen, Jeffrey L, Shi, Xiaodong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2010
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Chlorides - chemistry
Ferric Compounds - chemistry
Molecular Structure
Physical Sciences
Propanols - chemistry
Science & Technology
Stereoisomerism
Triazoles - chemical synthesis
Triazoles - chemistry
CYCLOADDITION
RECENT TRENDS
TRIAZOLE
CLICK CHEMISTRY
PROPARGYLIC ALCOHOLS
NUCLEOPHILIC-SUBSTITUTION
COMPLEXES
EFFICIENT SYNTHESIS
COORDINATION
ALKYNE ACTIVATION
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Summary:The FeCl3-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and regioselectivity, which could be applied as potential transition metal ligands or new reagents.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101082v