Synthesis 2018; 50(07): 1527-1534
DOI: 10.1055/s-0036-1589166
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient CuCl2-Catalyzed C–S Coupling of Aryl Iodides with Tetraalkylthiuram Disulfides: Synthesis of Aryl Dithiocarbamates

Autoren

  • Qiang Cao

    School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   eMail: dzb04982@wit.edu.cn
  • Han-Ying Peng

    School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   eMail: dzb04982@wit.edu.cn
  • Yu Cheng

    School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   eMail: dzb04982@wit.edu.cn
  • Zhi-Bing Dong*

    School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   eMail: dzb04982@wit.edu.cn

National Natural Science Foundation of China (21302150), Hubei Provincial Department of Education (D20131501), Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012]1707, foundation of Chutian distinguished fellow from Hubei Provincial Department of Education, foundation of High-end Talent Cultivation Program from Wuhan Institute of Technology. Z.-B. D. acknowledges the Humboldt Foundation and China Scholarship Council for a fellowship.
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Publikationsverlauf

Received: 21. November 2017

Accepted after revision: 10. Dezember 2017

Publikationsdatum:
11. Januar 2018 (online)


Graphical Abstract

These authors contributed equally to this work

Abstract

A highly efficient copper(II)-catalyzed C–S cross-coupling reaction of aryl iodides with tetraalkylthiuram disulfides was developed. With only 1 mol% of CuCl2 as catalyst, zinc powder as reductant, and K2CO3 as base, aryl iodides reacted with tetraalkylthiuram disulfides in DMSO furnishing the corresponding aryl dithiocarbamates in good to excellent yields. This protocol is an improvement of previous work, it features convenient performance, low addition of catalyst, no requirement for any ligand, and provides good yields. The method has a broad substrate scope and uses cheap and readily available starting materials.

Supporting Information