Revisiting the Electrochemical Carboxylation of Naphthalene with CO2: Selective Monocarboxylation of 2-Substituted Naphthalenes

Org Lett. 2023 Jun 16;25(23):4231-4235. doi: 10.1021/acs.orglett.3c01033. Epub 2023 Jun 2.

Abstract

Numerous remarkable reactions based on electrochemical carboxylations using CO2 have recently attracted considerable attention. In contrast to more recent examples, the electrochemical carboxylation of naphthalene had already been established in 1959, whereby a dearomative dicarboxylation selectively produces 1,4-dicarboxylated 1,4-dihydronaphthalene derivatives. Here, we report that the use of electron-deficient naphthalene derivatives in the presence of a redox mediator such as p-terphenyl and H2O under CO2 bubbling affords trans-1,2-disubstituted 1,2-dihydronaphthalene derivatives.

MeSH terms

  • Carbon Dioxide*
  • Naphthalenes*
  • Oxidation-Reduction

Substances

  • naphthalene
  • Carbon Dioxide
  • Naphthalenes