Synthesis, Table of Contents

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*

^aState Key Laboratory Breeding Base of Nuclear Resources and Environment, East China University of Technology, Nanchang 330013, P. R. of China

^bSchool 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

^bSchool 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

^bSchool 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

^bSchool 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

^bSchool 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*

^aState Key Laboratory Breeding Base of Nuclear Resources and Environment, East China University of Technology, Nanchang 330013, P. R. of China

^bSchool 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

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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.

Key words

Key words

cross-dehydrogenative coupling - copper - glycine ester - imidazo[1,2-a]pyridine - imine

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Supplementary Material

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Supporting Information