Pyrylium Salt Reagent for Nucleophilic Aromatic Substitution Reactions of Amino Heteroaromatic Compounds

Pyrylium tetrafluoroborate (1) is used in dehydrative condensation with the amino groups of amino heteroaromatic compounds to form pyridinium salts (2). Nucleophilic aromatic substitution reaction occurs when pyridinium salts are treated with nucleophiles like amines, alcohols, thiols, chlorides, fluorides, etc.^1,2) 2 can be used in a next step simply by concentration, requiring no further purifications. Functional group tolerance is high due to the mild conditions of the nucleophilic aromatic substitution reactions, making the late-stage functionalization of compounds like medicines possible. Furthermore, 1 can be used in the conversion of sulfonamides to sulfonyl fluorides.³⁾

Related Products

P2823

Pyrylium Tetrafluoroborate

T0055

Tetrabutylammonium Chloride

References

• 1) Deaminative chlorination of aminoheterocycles
  • C. Ghiazza, T. Faber, A. Gómez-Palomino, J. Cornella, Nat. Chem. 2022, 14, 78.
• 2) Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
  • D. Moser, Y. Duan, F. Wang, Y. Ma, M. J. O’Neill, J. Cornella, Angew. Chem. Int. Ed. 2018, 57, 11035.
• 3) Synthesis of Sulfonyl Fluorides from Sulfonamides
  • M. Pérez-Palau, J. Cornella, Eur. J. Org. Chem. 2020, 17, 2497.

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