Synthesis 2022; 54(02): 475-482
DOI: 10.1055/a-1645-6040
paper

Synthesis of Aryl Dithiocarbamates from Tetramethylthiuram Monosulfide (TMTM) and Aryl Boronic Acids: Copper-Catalyzed Construction of C(sp2)–S Bonds

Xu-Ling Xia
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Qi-Long Zhu
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Jin-Quan Chen
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Zhen Shi
b   Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University, Enshi 445000, P. R. of China
,
Zhi-Bing Dong
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
b   Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University, Enshi 445000, P. R. of China
c   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, P. R. of China
d   Key Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
› Author Affiliations
Financial support from the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (2020ZD02), the Key Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University (KFJJ2021008), and Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University (PT012101) is greatly appreciated. X.-L. X and Q.-L. Z. are grateful for support by the Principal’s Fund from the Wuhan Institute of Technology (2020116).


Abstract

A highly efficient method for the synthesis of S-aryl dithiocarbamates is reported. By using tetramethylthiuram monosulfide (TMTM) and aryl boronic acids as starting materials, C(sp2)–S bond-forming reactions proceed smoothly to give the desired aryl dithiocarbamates in good to excellent yields. The methodology features a simple procedure, broad functional group tolerance and excellent yields, whilst showing potential synthetic value for the preparation of a diverse range of biologically and pharmaceutically active compounds.

Supporting Information



Publication History

Received: 12 August 2021

Accepted after revision: 15 September 2021

Accepted Manuscript online:
15 September 2021

Article published online:
14 October 2021

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