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Synthesis 2018; 50(23): 4627-4636
DOI: 10.1055/s-0037-1610536
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Intermolecular Thioamination of Maleimides with Thiols and Formamides: A One-Step Construction of 3-Amino-4-thiomaleimides Using Formamides as Nitrogen Sources

Zhen-Hua Yang
a   Department of Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Jia-Nan Zhu
a   Department of Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Ze-Hui Jin
a   Department of Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Jian Zheng
a   Department of Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Sheng-Yin Zhao*
a   Department of Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
b   State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author AffiliationsThe authors acknowledge financial support from Shanghai Municipal Natural Science Foundation (No. 15ZR1401400), the Fundamental Research Funds for the Central Universities from the Ministry of Education of China (CUSF-DH-D-2015048 and CUSF-DH-D-2016028) and the National Innovation Experiment Program for University Students (17T10507) for financial support.
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Publication History

Received: 21 April 2018

Accepted after revision: 29 June 2018

Publication Date:
07 August 2018 (online)

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Abstract

A highly efficient copper-catalyzed intermolecular C(sp2)–H thioamination of maleimides with thiols and formamides in the presence of fluoroboric acid is reported using various readily available formamides as nitrogen sources and solvents. A diverse range of 3-amino-4-thiomaleimides is obtained with good yields under mild conditions, involving C–N and C–S bond formation. This methodology enriches current C–N and C–S bond formation chemistry and features operational simplicity and excellent functional-group tolerance.

Key words

copper catalysis - thioamination - maleimides - thiols - formamides

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