Synthesis 2018; 50(14): 2775-2783
DOI: 10.1055/s-0036-1609845
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines

Zhi-Qiang Zhu*
a  State Key Laboratory Breeding Base of Nuclear Resources and Environment, East China University of Technology, Nanchang 330013, P. R. of China
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
,
Li-Jin Xiao
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
,
Ying Chen
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
,
Zong-Bo Xie
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
,
Hai-Bo Zhu
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
,
Zhang-Gao Le*
a  State Key Laboratory Breeding Base of Nuclear Resources and Environment, East China University of Technology, Nanchang 330013, P. R. of China
b  School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.edu.cn   Email: zhgle@ecit.edu.cn
› Author Affiliations
Financial support from the National Natural Science Foundation of China (21602027, 11765003), the Natural Science Foundation of Jiangxi Province (20171BAB213006, 20171BAB203004), the China Postdoctoral Science Foundation (2018M632595), the Foundation of Jiangxi Educational Committee (GJJ170430) and the Scientific Research Foundation of East China University of Technology (DHBK2016112) are gratefully acknowledged.
Further Information

Publication History

Received: 06 February 2018

Accepted after revision: 08 April 2018

Publication Date:
28 May 2018 (online)


Abstract

A rapid and highly efficient copper(II)-catalyzed cross-dehydrogenative coupling (CDC) reaction of N-arylglycine esters with imidazo[1,2-a]pyridines has been described. A broad range of N-arylglycine esters underwent the CDC reaction smoothly with 2-arylimidazo[1,2-a]pyridines to give α-substituted α-amino acid esters in excellent yields. This synthetic method has the advantages of high yields, good functional groups compatibility, simple operation, and mild reaction conditions. A possible mechanism for the CDC reaction is also proposed. The use of a copper salt as the catalyst and air as the terminal oxidant makes this transformation sustainable and practical.

Supporting Information

 
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