4.7 Review

Recent advance in the C-F bond functionalization of trifluoromethyl-containing compounds

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 14, Pages 3915-3942

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00037c

Keywords

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Funding

  1. Natural Science Foundation of Zhejiang Province [LY18B020005]
  2. Lishui high-level talents training project [2017RC12]

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Activation of C-F bonds in trifluoromethyl-containing compounds is a challenging task in organic synthesis, with significant progress being made in the past decades mainly involving trifluoromethylalkenes, trifluoromethylated aromatic and alkyl compounds, among others.
The C-F bond is the strongest single bond in organic compounds. It is the most challenging task to study the activation of the C-F bond in organic synthesis. Trifluoromethyl-containing compounds, which have three equivalent C-F bonds, constitute possible starting materials for the synthesis of diverse fluorinated compounds through selective C-F bond activation. In the past decades, significant progress has been made in the C-F bond activation of trifluoromethyl-containing compounds, mainly including trifluoromethylalkenes, trifluoromethylated aromatic and alkyl compounds, trifluoromethylketones, diazo compounds and N-tosylhydrazones of trifluoromethyl ketones, alkyltriflones, etc. In this review, we systematically summarized the C-F bond functionalization of these trifluoromethylated compounds, and their mechanisms were also discussed.

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