Synthesis 2017; 49(18): 4303-4308
DOI: 10.1055/s-0036-1588460
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Chuancheng Zhang
a   School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, P. R. of China   eMail: dongli@mail.hbut.edu.cn
b   Department of Chemical and Environmental Engineering, Wuhan Institute of Bioengineering, Wuhan 430415, P. R. of China
,
Qiang Yue
a   School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, P. R. of China   eMail: dongli@mail.hbut.edu.cn
,
Zhen Xiao
a   School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, P. R. of China   eMail: dongli@mail.hbut.edu.cn
,
Xianglan Wang
b   Department of Chemical and Environmental Engineering, Wuhan Institute of Bioengineering, Wuhan 430415, P. R. of China
,
Qian Zhang
a   School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, P. R. of China   eMail: dongli@mail.hbut.edu.cn
,
Dong Li  *
a   School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, P. R. of China   eMail: dongli@mail.hbut.edu.cn
› Institutsangaben

We are grateful to the National Natural Science Foundation of China (NSFC, No. 21302046) and the Hundred-Talent Program Fund of Hubei University of Technology for financial support.
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Publikationsverlauf

Received: 28. März 2017

Accepted after revision: 19. Mai 2017

Publikationsdatum:
03. Juli 2017 (online)


Abstract

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

Supporting Information