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

Quan-Zhe Li; Xun-Hui Wang; Si-Hua Hou; Yan-Yan Ma; Deng-Gao Zhao; Shu-Yu Zhang; He-Yuan Bai; Tong-Mei Ding

doi:10.1055/s-0037-1610705

Synthesis, Table of Contents

Synthesis 2019; 51(13): 2697-2704
DOI: 10.1055/s-0037-1610705

special topic

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

Quan-Zhe Li

^aShanghai 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

^aShanghai 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

^aShanghai 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

^bSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China

,

Deng-Gao Zhao

^bSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China

,

Shu-Yu Zhang

^aShanghai 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*

^aShanghai 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*

^aShanghai 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

Abstract

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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.

Key words

transition metal - azodicarboxylates - regioselective - amination

Full Text

References

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Supplementary Material

Supporting Information

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

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