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Most Requested Journal Articles 1Q07-Chemistry and Related Science

Following is one of the journal articles most requested by researchers using CAS electronic products.

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CAS indexed 121 chemical substances from this document. CAS subject entries for this document include: Amines, preparation; Ullmann reaction; Ullmann reaction catalysts; and 3 additional concepts.

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TITLE:	Amino Acid Promoted CuI-Catalyzed C-N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles
AUTHOR(S):	Zhang, Hui; Cai, Qian; Ma, Dawei
CORPORATE SOURCE:	Department of Chemistry, Fudan University, Shanghai, 200433, Peop. Rep. China
SOURCE:	Journal of Organic Chemistry (2005), 70(13), 5164-5173 CODEN: JOCEAH; ISSN: 0022-3263
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
CuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliph. primary amines occurred under the promotion of N-methylglycine. Using L-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliph. primary amines, aliph. cyclic secondary amines, or electron-rich primary arylamines proceeded. Also, an intramol. coupling reaction between aryl chloride and primary amine moieties gave indoline. Coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole was also carried out. And, finally, coupling of electron-deficient aryl bromides with imidazole or pyrazole occurred. The corresponding N-aryl products were obtained in good to excellent yields. N,N-dimethylglycine promoted the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles. The possible action of amino acids in these coupling reactions is discussed.