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Synthesis 2018; 50(20): 4113-4123
DOI: 10.1055/s-0037-1609585
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Promoted C(sp 2)–H Thiolation of Maleimides with Dimethyl Sulfoxide and Thiols

Hong-Ru Tan
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
,
Lun Wang
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
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
,
Zhen-Hua Yang
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*
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
› Author AffiliationsWe acknowledge the financial support from Shanghai Municipal Natural Science Foundation (No. 15ZR1401400) and Advanced Organic Chemistry Experimental Reform Foundation (17T10513).
Further Information

Publication History

Received: 12 June 2018

Accepted after revision: 21 June 2018

Publication Date:
30 July 2018 (online)

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§ Hong-Ru Tan and Lun Wang contributed equally to this work.

Abstract

Iodine-promoted C(sp 2)–H methylthiolation of maleimides using DMSO as synthon has been developed to afford 3-methylthiomaleimides in moderate yields under metal-free conditions. In addition, 3-thiomaleimides were synthesized from maleimides and thiols in the presence of iodine and triethylamine. The methods are simple and efficient for the formation of C–S bond.

Key words

iodine - thiolation - maleimide - DMSO - thiol

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609585.
  • Supporting Information
 

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