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Updated: Jan 31, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Cyclic Imine-BF3 Complexes as Precursors for Functionalized Azacycles.

Kamal Bhatt1, Daniel Seidel1

  • 1Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|January 30, 2026
PubMed
Summary
This summary is machine-generated.

Stable BF3 adducts of enolizable alicyclic imines simplify functionalized amine synthesis, eliminating the need for cryogenic temperatures. These adducts serve as versatile building blocks for complex azacycles.

Keywords:
Imine-BF3 complexesacridinesalicyclic aminesphotocatalysisradical additions

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Enolizable alicyclic imines are typically unstable and exhibit low electrophilicity.
  • Their functionalization often necessitates cryogenic temperatures and potent nucleophiles like organolithium compounds.

Purpose of the Study:

  • To develop a more efficient method for functionalizing enolizable alicyclic imines.
  • To explore the use of stable boron trifluoride (BF3) adducts as synthetic intermediates.

Main Methods:

  • Formation of stable BF3 adducts with enolizable alicyclic imines.
  • Utilizing these adducts in reactions with various nucleophiles, including organometallic and radical-centered reagents.
  • Assessing the stability and storage potential of the imine-BF3 complexes.

Main Results:

  • The imine-BF3 adducts are stable and can be stored for extended periods (over a year in some cases).
  • These adducts facilitate the synthesis of functionalized amines without requiring cryogenic conditions.
  • The complexes demonstrate compatibility with a range of nucleophiles, enabling diverse functionalization.

Conclusions:

  • Stable imine-BF3 adducts offer a streamlined and practical approach to synthesizing functionalized amines.
  • These complexes are valuable building blocks for constructing functionalized azacycles.
  • The method broadens the scope of imine functionalization, avoiding harsh reaction conditions.