- Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide
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We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.
- Okumura, Shintaro,Uozumi, Yasuhiro
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supporting information
p. 7194 - 7198
(2021/09/22)
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- Syntheses of Benzilic Acids through Electrochemical Reductive Carboxylation of Benzophenones in the Presence of Carbon Dioxide
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Reaction conditions for the electrochemical synthesis of benzilic acid (2a) under the atmosphere of carbon dioxide was investigated from the preparative points of view.The highest yield of 2a (86percent) was obtained under the following conditions; cathode: mercury, electricity passed: 2.3 F/mol, constant current density: 2.5 mA/cm2, benzophenone (1a) (8.2*10-3 mol), electrolyte(KI, 1.7*10-2 mol) in DNF (50 ml).This method and conditions were applied to the syntheses of twelve benzilic acids (2b-2m) and yielded acids in the range of 10-92percent.The yields were strongly depended on the electronic effect of substituents and benzilic acids were not obtained when the ring substituent was NO2, OH, or Br group.
- Ikeda, Yoshikazu,Manda, Eiichiro
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p. 1723 - 1726
(2007/10/02)
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