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DOI: 10.1055/a-1649-5460
Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles
This work was financed by the OPUS 16 program of the National Science Centre, Poland (Narodowe Centrum Nauki; UMO-2018/31/B/ST5/01118).
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Abstract
A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7–20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1649-5460.
- Supporting Information
Publication History
Received: 10 September 2021
Accepted after revision: 20 September 2021
Accepted Manuscript online:
20 September 2021
Article published online:
16 November 2021
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For recent reviews on application of acyl fluorides, see:
For selected examples of application of acyl fluorides in metal-catalyzed transformations, see:
Interesting alternative to the inorganic fluorides is the application of HF or its pyridine complex; however, both are considered highly corrosive species:
For the preparation and properties of extremely hindered tertiary amines, see: