The silver(I)‐mediated decarboxylative fluorination of paraconic acids using Selectfluor® as a fluorine source is reported. Readily available paraconic acids undergo decarboxylative fluorination with Selectfluor® mediated by AgNO3 to give the corresponding β‐fluorinated γ‐butyrolactones in moderate to good yields. This approach serves as a direct and site‐selective strategy for the introduction of a fluorine atom at the β position of γ‐butyrolactone cores. The fluorinated products are synthetically useful scaffolds for organic synthesis.
Monofluorinated cyclic nitrogen‐containing compounds are synthetically useful scaffolds in organic synthesis and medicinal applications. In this report, AgNO3 mediated decarboxylative fluorination of β‐carboxyl‐γ‐butyrolactams using Selectfluor® as a fluorine source was described to achieve a site‐specific synthesis of β‐fluorinated γ‐butyrolactams.
A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.
Silver-Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to -Fluorinated -Butyrolactones. -(PHAE-NOK, S.; SOORUKRAM*, D.; KUHAKARN, C.; REUTRAKUL, V.; POHMAKOTR, M.; Eur. J. Org. Chem. 2015, 13, 2879-2888, http://dx.
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