Synthesis 2017; 49(23): 5120-5130
DOI: 10.1055/s-0036-1590893
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed C–N Bond Exchange of N-Heterocyclic Substituents around Pyridine and Pyrimidine Cores

Sheng Tao
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
,
Enhui Ji
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
,
Lei Shi
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
,
Ning Liu  *
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
,
Liang Xu*
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
,
Bin Dai*
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China   Email: ninglau@163.com   Email: ningliu@shzu.edu.cn   Email: xuliang4423@163.com   Email: dbinly@126.com
› Author Affiliations
The authors thank the National Natural Science Foundation of China for financial support (grant number 21466033), the Program for Changjiang Scholars and Innovative Research Team in University (Grant No. IRT_15R46), and Yangtze River scholar research project of Shihezi University (Grant No. CJXZ201601).
Further Information

Publication History

Received: 02 May 2017

Accepted after revision: 03 August 2017

Publication Date:
28 August 2017 (online)


S. Tao and E. Ji contributed equally.

Abstract

A copper-catalyzed transfer N-heteroarylation strategy using a C–N bond exchange reaction is described. This reaction accommodates a wide range of pyridine and pyrimidine rings bearing halogen atoms, which have wide utility for subsequent transformations. This method provides a direct and operationally simple approach for modifying complex molecules by the exchange of N-heterocyclic substituents.

Supporting Information

 
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