Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System.

A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO3- was disclosed, which was generated from esterification between the in situ generated HSO4- and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO3- and aldehydes. The ionic oxidant 1a ((NH4)2S2O8) with more N-H numbers in the cation, as compared with 1c ((n-Bu4N)2S2O8) and 1d ((PyH)2S2O8), has better performance in the oxidative esterification of aldehydes.

• Publication year

  2017

• Venue

  Journal of Organic Chemistry

• Publication date

  2017-01-23

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.joc.6b02775PMID 28111951
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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