Synthesis 2020; 52(02): 239-245
DOI: 10.1055/s-0039-1690220
paper
© Georg Thieme Verlag Stuttgart · New York

Silver-Promoted Regioselective Oxidative Decarboxylative C–H Alkylation of Phenanthridines with Carboxylic Acids

Tianyin Huang
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Yang Yu
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Hui Wang
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Yifan Lin
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Yurui Ma
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Haoyu Wang
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Junjie Xiao
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
,
Bin Xu
a   Department of Chemistry, Innovative Drug Research Center, Qianweichang College, School of Life Science, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn   Email: junjiexiao@live.cn   Email: xubin@shu.edu.cn
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author Affiliations
We thank the National Natural Science Foundation of China (No. 21672136, 21871174, 21772215) and Innovation Program of Shanghai Municipal Education Commission (No. 2019-01-07-00-09-E00008) for financial support.
Further Information

Publication History

Received: 12 September 2019

Accepted after revision: 02 October 2019

Publication Date:
29 October 2019 (online)


§ These authors contributed equally to this manuscript

Abstract

A novel oxidative decarboxylative C–H alkylation of phenanthridines with carboxylic acids was developed for the efficient synthesis of multi-substituted phenanthridine derivatives. The given method features easy availability of starting materials, high regioselectivity, and mild conditions. Furthermore, a one-pot synthesis of multi-substituted phenanthridine derivatives was realized by the reaction of biphenyl isocyanides and carboxylic acid.

Supporting Information