A Convenient, One-Pot Procedure for the Preparation of Acyl and Sulfonyl Fluorides Using Cl₃CCN, Ph₃P, and TBAF(t-BuOH)₄

Abstract

Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)₄ at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement.

Key words

carboxylic acid - acyl fluoride - sulfonyl fluoride - amino acid fluoride - trichloroacetonitrile

References and Notes

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20

Typical experimental procedure: To a mixture of benzoic acid (1.22 g, 10 mmol) and Ph₃P (5.26 g, 20 mmol) in MeCN (25 mL) under argon, was added Cl₃CCN (2 mL, 20 mmol) dropwise at r.t. The reaction mixture was stirred at r.t. for
1 h. TBAF(t-BuOH)₄ (11.2 g, 20 mmol) was added to the above solution, and stirring was continued for 1 h at r.t. After concentration of the reaction mixture by using a rotary evaporator, the residue was purified by distillation under reduced pressure to give benzoyl fluoride (1.12 g, 91%;
bp 88-90 ˚C/100 mmHg (Lit.^¹³c 84-86 ˚C/98 mmHg).