Synthesis 2019; 51(13): 2697-2704
DOI: 10.1055/s-0037-1610705
special topic
© Georg Thieme Verlag Stuttgart · New York

Silver-Catalyzed para-Selective C–H Amination of 1-Naphthyl­amides with Azodicarboxylates at Room Temperature

Quan-Zhe Li
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Xun-Hui Wang
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Si-Hua Hou
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Yan-Yan Ma
b   School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China
,
Deng-Gao Zhao
b   School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China
,
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
He-Yuan Bai*
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Tong-Mei Ding*
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
› Author Affiliations
This work was supported by the NSFC (No. 21672145, No. 21602131), Shanghai Jiao Tong University (No. ZH2018QNA44, No. IPP18080) and Department of Education of Guangdong Province (No. 2016KTSCX140).
Further Information

Publication History

Received: 13 February 2019

Accepted after revision: 19 March 2019

Publication Date:
11 April 2019 (online)


Published as part of the Special Topic Amination Reactions in Organic Synthesis

Abstract

A simple and efficient protocol for para-selective C–H amination of 1-naphthylamide derivatives under silver catalysis is described. This reaction system could proceed without the help of directing group and a broad range of substrates were proved to be well tolerated. In addition, control experiments suggested that this reaction might not proceed via a single-electron-transfer process.

Supporting Information