Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis

Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, e...

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Published inPure and applied chemistry Vol. 81; no. 2; pp. 227 - 234
Main Authors Cai, Qian, Zhang, Hui, Zou, Benli, Xie, Xiaoan, Zhu, Wei, He, Gang, Wang, Jing, Pan, Xianhua, Chen, Yu, Yuan, Qiliang, Liu, Feng, Lu, Biao, Ma, Dawei
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.01.2009
Walter de Gruyter GmbH
Subjects
Amino acids
Aromatic compounds
catalysis
Chemical reactions
Chemical synthesis
copper
Coupling
Halides
Phenols
Reagents
Substitution reactions
Substrates
synthesis
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Summary:Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, either as substrates or ligands, can lead Cu-catalyzed C-N, C-O, C-S, and C-C bond formations work at relatively low temperatures. An -substitution effect caused by NHCOR groups is discussed. Applications of these newly developed reactions to heterocycle preparation and asymmetric synthesis are also presented.
ISSN:0033-4545
1365-3075
DOI:10.1351/PAC-CON-08-08-19