S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Shuilin Deng; Haohua Chen; Xingxing Ma; Yao Zhou; Kai Yang; Yu Lan; Qiuling Song

doi:10.1039/c9sc01333d

S₈-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Chem Sci. 2019 Jun 5;10(28):6828-6833. doi: 10.1039/c9sc01333d. eCollection 2019 Jul 28.

Authors

Shuilin Deng¹, Haohua Chen², Xingxing Ma¹, Yao Zhou¹, Kai Yang³, Yu Lan^{2

4}, Qiuling Song^{1

3

5}

Affiliations

¹ Institute of Next Generation Matter Transformation , College of Chemical Engineering , College of Material Sciences Engineering at Huaqiao University , 668 Jimei Boulevard , Xiamen , Fujian 361021 , China . Email: qsong@hqu.edu.cn.
² School of Chemistry and Chemical Engineering , Chongqing University , Chongqing 400030 , P. R. China.
³ College of Chemistry , Fuzhou University , Fuzhou , Fujian 350108 , China.
⁴ College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou 450001 , P. R. China.
⁵ State Key Laboratroy of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , Shanghai 200032 , P. R. China.

Abstract

An unprecedented S₈-catalyzed selective triple-cleavage of bromodifluoroacetamides is disclosed for the first time. Valuable 2-amido substituted benzimidazoles, benzoxazoles and benzothiazoles were obtained in good to excellent yields in a cascade protocol in this strategy. Mechanistic studies suggested that a C2 source was generated in situ by selective cleavage of three C-X bonds, including two inert C(sp³)-F bonds on bromodifluoroacetamides, while leaving C-C bonds intact. This strategy will undoubtedly further consummate the role of halo difluoro compounds and enrich both fluorine chemistry and pharmaceutical sciences.