Visible-Light-Driven Reductive Carboxylation of Benzyl Bromides with Carbon Dioxide Using Formate as Terminal Reductant.
J Org Chem
; 88(8): 5007-5014, 2023 Apr 21.
Article
em En
| MEDLINE
| ID: mdl-36126282
ABSTRACT
Cheap and available formate can be seen formally as a carbon dioxide radical anion (CO2â¢-) combined with a hydrogen atom, where the CO2â¢- is not only a highly active radical but also a very powerful reductant. In this paper, we successfully realized a visible-light-driven carboxylation of benzyl bromides with carbon dioxide to prepare high-value arylacetic acids using potassium formate as a terminal reductant. This reaction is characterized by mild reaction conditions and a wide range of substrates. Moreover, under nitrogen atmosphere, the reaction can also achieve the carboxylation of benzyl bromides utilizing an excess of potassium formate. Mechanistic experiments indicate this carboxylation proceeded through CO2â¢-, which was generated from the oxidation of 1,4-diazabicyclo[2.2.2]octane with excited photosensitizer Ir(ppy)2(dtbbpy)PF6 in the presence of the potassium formate.
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MEDLINE
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En
Ano de publicação:
2023
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Article