trans-Trifluoromethyltetrafluorosulfanyl Chloride: Selective Synthesis and Reaction with Diazo Compounds

Xin Zhao; Jia-Yi Shou; Josiah J Newton; Feng-Ling Qing

doi:10.1021/acs.orglett.2c03540

trans-Trifluoromethyltetrafluorosulfanyl Chloride: Selective Synthesis and Reaction with Diazo Compounds

Org Lett. 2022 Nov 18;24(45):8412-8416. doi: 10.1021/acs.orglett.2c03540. Epub 2022 Nov 4.

Authors

Xin Zhao¹, Jia-Yi Shou¹, Josiah J Newton², Feng-Ling Qing¹

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
² Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC V5A 1S6, Canada.

PMID: 36331806
DOI: 10.1021/acs.orglett.2c03540

Abstract

trans-Trifluoromethyltetrafluorosulfanyl chloride (trans-CF₃SF₄Cl) is a unique reagent for the incorporation of the CF₃SF₄ group into organic compounds. However, CF₃SF₄Cl was prepared from hazardous reagents or formed as mixture of trans and cis isomers in low yield. Herein, a silver-promoted selective synthesis of trans-CF₃SF₄Cl under safe gas-reagent-free conditions is described. Furthermore, the synthetic application of trans-CF₃SF₄Cl is demonstrated through the new trifluoromethyltetrafluorosulfanylation of α-diazo carbonyl compounds.