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Synlett 2019; 30(19): 2169-2172
DOI: 10.1055/s-0039-1690237
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions

Yao-Fu Zeng
a   Institute of Pharmacy and Pharmacology, University of South China, Hengyang, 421001, P. R. of China   Email: zengyf@usc.edu.cn
b   School of Pharmaceutical Science, University of South China, Hengyang, 421001, P. R. of China
,
Yi-Na Li
a   Institute of Pharmacy and Pharmacology, University of South China, Hengyang, 421001, P. R. of China   Email: zengyf@usc.edu.cn
,
Na-Na Zhang
b   School of Pharmaceutical Science, University of South China, Hengyang, 421001, P. R. of China
,
Huan Kang
b   School of Pharmaceutical Science, University of South China, Hengyang, 421001, P. R. of China
,
Pan Duan
b   School of Pharmaceutical Science, University of South China, Hengyang, 421001, P. R. of China
,
Fang Xiao
a   Institute of Pharmacy and Pharmacology, University of South China, Hengyang, 421001, P. R. of China   Email: zengyf@usc.edu.cn
,
Yu Guo
a   Institute of Pharmacy and Pharmacology, University of South China, Hengyang, 421001, P. R. of China   Email: zengyf@usc.edu.cn
b   School of Pharmaceutical Science, University of South China, Hengyang, 421001, P. R. of China
,
Xianghao Wen∗
c   Affiliated Nanhua Hospital, University of South China, Hengyang, 421001, P. R. of China
› Author AffiliationsThis research was supported by the "Double First-Class" Discipline Construction Foundation of the University of South China (2017SYL06), the Undergraduate Training Programs for Innovation and Entrepreneurship in Hunan Province (S201910555144), and the Foundation of Hunan Educational Committee (18C0476, 18C0467).
Further Information

Publication History

Received: 27 July 2019

Accepted after revision: 15 October 2019

Publication Date:
23 October 2019 (online)

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Abstract

An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

Key words

aryl amines - amidation - acetonitrile - diazotization - acetamides - coupling reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690237.
  • Supporting Information
 

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