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Synlett 2017; 28(11): 1321-1326
DOI: 10.1055/s-0036-1588760
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Highly Efficient Esterification of Aldehydes with N-Hydroxyphthalimide via Cross-Dehydrogenative Coupling in Water at Room Temperature

Zhicheng Guo
a   Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: pharmlab@zjut.edu.cn
,
Xinpeng Jiang
b   College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jincan@zjut.edu.cn
,
Can Jin*
b   College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jincan@zjut.edu.cn
,
Jiadi Zhou
a   Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: pharmlab@zjut.edu.cn
,
Bin Sun
a   Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: pharmlab@zjut.edu.cn
,
Weike Su*
a   Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: pharmlab@zjut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 18 January 2017

Accepted after revision: 27 February 2017

Publication Date:
27 March 2017 (online)

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Abstract

A copper-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide and aldehydes using PhI(OAc)2 as an oxidant is described. It is reported for the first time to synthesize NHPI esters in water, providing the corresponding NHPI esters in moderate to good yields. This facile and efficient method is eco-friendly and possesses the advantages of mild conditions, short reaction time, and broad substrate scope.

Key words

copper-catalyzed - esterification - cross-dehydrogenative coupling reaction - water - NHPI esters

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588760.
  • Supporting Information
 

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