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January 22, 2026Organic Letters0 citations

Temperature Dependent Divergent Radical Oxidative Amidation Engaging Arylglyoxyl Radicals

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PBPratibha BhattiAGAnjali GuptaSCShubham Chaudhari

Key Points

  • The research aims to explore the synthesis of arylglyoxyl amides and aromatic amides through a new radical oxidative amidation process.
  • Generated arylglyoxyl radicals from arylglyoxals in situ.
  • Utilized tert-butyl hydroperoxide and iodine as catalysts.
  • Conducted reactions at two different temperatures (120 °C and 180 °C).
  • Examined the reaction outcomes with various amines.
  • At 120 °C, arylglyoxyl amides were formed.
  • At 180 °C, aromatic amides were synthesized.
  • Decarbonylation at higher temperature generated aroyl radicals for further reactions.

Abstract

The present study reports the divergent reaction of previously underexplored arylglyoxyl radicals generated in situ from arylglyoxals in the presence of tert-butyl hydroperoxide (TBHP) and a catalytic amount of iodine with various amines at two different temperatures leading to the synthesis of arylglyoxal amides at 120 °C and aromatic amides at 180 °C. The two radicals, arylglyoxyl radical and aroyl radical, generated via decarbonylation at higher temperature, could react with amines via radical polar crossover.

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Cite This Study

Bhatti et al. (2026) studied this question.

synapsesocial.com/papers/6971bfdff17b5dc6da021f22https://doi.org/10.1021/acs.orglett.5c04569
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