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

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

doi:10.1351/PAC-CON-08-08-19

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

http://dx.doi.org/10.1351/PAC-CON-08-08-19

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.