Synlett 2018; 29(01): 79-84
DOI: 10.1055/s-0036-1591210
letter
© Georg Thieme Verlag Stuttgart · New York

Copper(I) Iodide-Catalyzed (Het)arylation of Diethyl Malonate with (Het)aryl Bromides by Using 1,3-Benzoxazole as a Ligand

Yu Zeng
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing, 211816, P. R. of China   Email: fzcpu@163.com   Email: guok@njtech.edu.cn
,
Hao-liang Zheng
b   School of Chemistry and Molecular Biosciences, Faculty of Chemistry, The University of Queensland, Brisbane, Queensland, Australia
,
Zhao Yang
c   College of Engineering, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing, 210003, P. R. of China
,
Cheng-Kou Liu
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing, 211816, P. R. of China   Email: fzcpu@163.com   Email: guok@njtech.edu.cn
,
Zheng Fang*
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing, 211816, P. R. of China   Email: fzcpu@163.com   Email: guok@njtech.edu.cn
,
Kai Guo*
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing, 211816, P. R. of China   Email: fzcpu@163.com   Email: guok@njtech.edu.cn
d   State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing, 211816, P. R. of China
› Author Affiliations
The research has been supported by National Natural Science Foundation of China (Grant No.U1463201, 21522604 and 21402240) and ­Jiangsu Province Natural Science Fund (Grant No.BK20150031)
Further Information

Publication History

Received: 20 June 2017

Accepted after revision: 26 July 2017

Publication Date:
26 October 2017 (online)


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Abstract

An efficient Ullmann-type coupling of aryl bromides with diethyl malonate in the presence of copper(I) iodide and 1,3-benzoxazole is presented. This method has a broad substrate scope (heterocyclic and phenyl bromides) and good functional-group tolerance (OMe, Me, Ac, CN, NO2, F, and Cl). Moreover, less time is needed to reach full conversion (3–9 hours).

Supporting Information