4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 3, Pages 319-322

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc06004f

Keywords

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Funding

  1. Natural Science Foundation of China [21632009, 214210025]
  2. Key Programs of the Chinese Academy of Sciences [KGZDEWT08]
  3. Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH049]
  4. Shanghai Science and Technology Program [18JC1410601]
  5. Natural Science Foundation of Zhejiang Province [LY18B020003, LY18B020002]
  6. Chemical Engineering & Technology of Zhejiang Province FirstClass Discipline (Taizhou University)

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

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