Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Abstract

Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β position as their characteristic functionality, using a combination of AgNO3/K2S2O8 was investigated. The dual function of AgNO3 as an initiator for decarboxylation process and a nitrogen dioxide radical source that reacts with aliphatic carboxylic substrates of this study was reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41-85% yields) with moderate selectivity in one-pot operation. The reactions completed within acceptable reaction time (2 h) under mild reaction conditions that γ-butyrolactone core could be tolerated. The present study represents the direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones which are important precursors in organic transformations.

Radical Decarboxylative Carbon–Nitrogen Bond Formation

“…The final cross-coupling product would be generated via nucleophilic attack. In 2022, the Soorukram group reported that the combined AgNO 3 /K 2 S 2 O 8 system can be used for radical decarboxylative transformations of paraconic acids (Scheme 9) [51]. Under oxidative conditions, a range of paraconic acids can be used as the substrates, and a mixture of β-nitro and β-hydroxy γ-butyrolactones was produced.…”

“… AgNO 3 /K 2 S 2 O 8 –mediated radical decarboxylative transformations of paraconic acids (Soorukram et al, 2022 [ 51 ]). …”