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Synlett 2015; 26(18): 2557-2560
DOI: 10.1055/s-0035-1560180
letter
© Georg Thieme Verlag Stuttgart · New York

MnO2-Catalyzed Oxidative Alkylation of Enamides with Ethers via C(sp3)–H/C(sp2)–H Cross-Dehydrogenative Coupling and Hydrolysis Sequence

Zhiyan Hu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
b   Key Laboratory of Chemical Ultilization of Forestry Biomass of Zhejiang Province, School of Science Zhejiang Agriculture and Forestry University, Lin’an 311300, P. R. of China
,
Yucai Tang
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
,
Shan Zhang
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
,
Xiaoqing Li
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
,
Xiaohua Du
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
,
Xiangsheng Xu*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: future@zjut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 25 May 2015

Accepted after revision: 23 July 2015

Publication Date:
02 September 2015 (online)

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Abstract

A new MnO2-catalyzed oxidative alkylation of enamides with a C(sp3)–H bond adjacent to an oxygen atom is described. This method achieves a C(sp3)-H/C(sp2)-H cross-dehydrogenative coupling and hydrolysis, thus providing efficient and general access to a variety of β-oxo ketones.

Key words

C(sp3)–H/C(sp2)–H cross-dehydrogenative coupling - ethers - enamides - β-oxo ketones - radicals

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560180.
  • Supporting Information
 

  • References and Notes


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