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Synlett 2019; 30(18): 2096-2100
DOI: 10.1055/s-0039-1690697
letter
© Georg Thieme Verlag Stuttgart · New York

Silver-Promoted Versatile Cross-Dehydrogenative Coupling of Quinaldine with Usual Ethers

Shoufeng Wang∗
a   School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China   Email: chm_wangsf@ujn.edu.cn   Email: chm_wangwg@ujn.edu.cn
b   Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical materials, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China
,
Yafei Fan
a   School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China   Email: chm_wangsf@ujn.edu.cn   Email: chm_wangwg@ujn.edu.cn
b   Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical materials, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China
,
Huaiqing Zhao
a   School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China   Email: chm_wangsf@ujn.edu.cn   Email: chm_wangwg@ujn.edu.cn
c   Key Laboratory of Interfacial Reaction & Sensing Analysis in Universities of Shandong, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China
,
Jianfeng Wang
d   Department of Respiratory Diseases, the Affiliated Hospital of Hangzhou Normal University, Hangzhou, Zhejiang, 310015, P. R. of China
,
Shuxiang Zhang
a   School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China   Email: chm_wangsf@ujn.edu.cn   Email: chm_wangwg@ujn.edu.cn
b   Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical materials, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China
,
Wengui Wang  ∗
a   School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China   Email: chm_wangsf@ujn.edu.cn   Email: chm_wangwg@ujn.edu.cn
b   Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical materials, 336 West Road of Nan Xinzhuang, Jinan, 250022, P. R. of China
› Author AffiliationsFinancial support from the Shandong Provincial Natural Science Foundation (Grant numbers ZR2016HM44, ZR2016BQ31, and ZR2016JL009), the Shandong Key Research Program (Grant number 2017GSF218061), the Major Program of Shandong Province Natural Science Foundation (Grant number ZR2017ZC0529) of China and University of Jinan is gratefully acknowledged.
Further Information

Publication History

Received: 01 July 2019

Accepted after revision: 18 September 2019

Publication Date:
07 October 2019 (online)

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Abstract

The application of small molecules as synthetic blocks is a field of great meaning and full of challenges, especially the use of inert ether molecules, such as THF as starting materials. A versatile and easily handled cross-dehydrogenative coupling between ethers and quinaldine is reported here. Compared to the developed reaction, Selectfluor is used as a mild oxidant, and a variety of functional groups are tolerated. Nitrogen protection, anhydrous systems, and external base are not needed, making this method a convenient route to functional heterocycles.

Key words

cross-dehydrogenative coupling - Selectfluor - quinaldine - ethers - silver

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690697.
  • Supporting Information
 

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