Sulfite-Promoted Synthesis of N-Difluoromethylthioureas via the Reaction of Azoles with Bromodifluoroacetate and Elemental Sulfur

Jian-Chao Deng; Yong-Chao Gao; Zhu Zhu; Li Xu; Zhao-Dong Li; Ri-Yuan Tang

doi:10.1021/acs.orglett.8b03876

Sulfite-Promoted Synthesis of N-Difluoromethylthioureas via the Reaction of Azoles with Bromodifluoroacetate and Elemental Sulfur

Org Lett. 2019 Jan 18;21(2):545-548. doi: 10.1021/acs.orglett.8b03876. Epub 2018 Dec 31.

Authors

Jian-Chao Deng¹, Yong-Chao Gao¹, Zhu Zhu¹, Li Xu¹, Zhao-Dong Li¹, Ri-Yuan Tang^{1

2}

Affiliations

¹ Department of Applied Chemistry, College of Materials and Energy , South China Agricultural University , Guangzhou 510642 , China.
² Key Laboratory of Natural Pesticide & Chemical Biology, Ministry of Education , South China Agricultural University , Guangzhou 510642 , China.

PMID: 30596506
DOI: 10.1021/acs.orglett.8b03876

Abstract

A sulfite-promoted transformation of azoles into N-difluoromethylthioureas through N-difluoromethylation and sulfuration has been developed. In this reaction, inexpensive ethyl bromodifluoroacetate and nontoxic elemental sulfur were used as the difluoromethylation and sulfuration reagents, respectively. A variety of azoles, including benzimidazoles, imidazoles, and triazoles, performed well to afford a broad range of azole thioureas in moderate to good yields.

Publication types

Research Support, Non-U.S. Gov't