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Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 227-234

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

Qian Cai1, Hui Zhang2, Benli Zou2, Xiaoan Xie2, Wei Zhu2, Gang He1, Jing Wang1, Xianhua Pan2, Yu Chen2, Qiliang Yuan2, Feng Liu1, Biao Lu1 and Dawei Ma1

1 State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China
2 Department of Chemistry, Fudan University, Shanghai 200433, China

Abstract: 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 ortho-substitution effect caused by NHCOR groups is discussed. Applications of these newly developed reactions to heterocycle preparation and asymmetric synthesis are also presented.