CuI-Catalyzed Amination of Arylhalides with Guanidines or Amidines: A Facile Synthesis of 1-H-2-Substituted Benzimidazoles

CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-amino-benzimidazoles through tandem aminations of 1,2-dihaloarenes in modest yiel...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 74; no. 15; pp. 5742 - 5745
Main Authors Deng, Xiaohu, McAllister, Heather, Mani, Neelakandha S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2009
Amer Chemical Soc
Subjects
Amidines - chemistry
Amination
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Ethylenediamines - chemistry
Guanidine - chemistry
Hydrocarbons, Halogenated - chemistry
Iodides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
POTENT
CASCADE REACTIONS
HETEROCYCLES
ARYL HALIDES
HYDROCHLORIDES
N BOND FORMATION
IMIDAZOLES
VINYL HALIDES
ANTAGONISTS
EFFICIENT METHOD
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Summary:CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-amino-benzimidazoles through tandem aminations of 1,2-dihaloarenes in modest yields. This methodology is also applicable for the preparation of 1-H or 1-substutituted 2-aryl- or 2-alkyl-benzimidazoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo900912h