Coupling Reactions of Bromoalkynes with Imidazoles Mediated by Copper Salts: Synthesis of Novel N-Alkynylimidazoles

A cross-coupling reaction of imidazoles with bromoalkynes in the presence of a catalytic amount of CuI is reported. This protocol allows an access to novel N-(1-alkynyl)imidazoles in moderate to good yields.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 73; no. 16; pp. 6462 - 6465
Main Authors Laroche, Christophe, Li, Jing, Freyer, Matthew W, Kerwin, Sean M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.08.2008
Amer Chemical Soc
Subjects
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrocarbons, Brominated - chemistry
Imidazoles - chemical synthesis
Imidazoles - chemistry
Iodides - chemistry
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
O-ARYLATION
HETEROCYCLES
EQUILIBRIA
CHIRAL YNAMIDES
ARYL HALIDES
COMPLEXES
AMIDATION
LIGAND
EFFICIENT
YNAMINES
Imidazole derivatives
Catalytic reaction
Acetylenic compound
Nitrogen heterocycle
Cross reaction
Copper I Iodides
Chemical synthesis
Chemical coupling
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Summary:A cross-coupling reaction of imidazoles with bromoalkynes in the presence of a catalytic amount of CuI is reported. This protocol allows an access to novel N-(1-alkynyl)imidazoles in moderate to good yields.
Bibliography:ark:/67375/TPS-R4LQBGLX-G
General procedure for bromoalkyne preparation, characterization data, and 1H NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801118q