TMSCFX2 (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes

Dingben Chen; Zili Fan; Ling Huang; Kaili Gao; Pan Xiao; Chuanfa Ni; Jinbo Hu

doi:10.1039/d0cc06004f

TMSCFX₂ (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes

Chem Commun (Camb). 2021 Jan 14;57(3):319-322. doi: 10.1039/d0cc06004f.

Authors

Dingben Chen¹, Zili Fan, Ling Huang, Kaili Gao, Pan Xiao, Chuanfa Ni, Jinbo Hu

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. jinbohu@sioc.ac.cn.

PMID: 33326515
DOI: 10.1039/d0cc06004f

Abstract

TMSCFX2 (X = Cl, Br; TMS = trimethylsilyl) have been developed as halofluorocarbene (CFX, X = Cl, Br) precursors for [2+1] cyclopropanation with alkenes. Structurally diverse halofluorocyclopropanes were obtained in good to excellent yields. It was found that the reactivity order of the three halofluorocarbene reagents (TMSCF2Br, TMSCFCl2, and TMSCFBr2) in halofluorocyclopropanation with 1,1-diphenylethylene can be very different under different reaction conditions.