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Organophotocatalytic oxidation of alcohols to carboxylic acids
Shrikant D. Tambe,Eun Jin Cho 대한화학회 2022 Bulletin of the Korean Chemical Society Vol.43 No.11
A sustainable photochemical protocol for the oxidation of alcohols to ketonesand carboxylic acids has been developed by using 2,4,6-triphenylpyrylium tetrafluoroborate(TPPT) as organophotocatalyst and molecular oxygen as oxidantunder visible light irradiation. The key reactive oxygen species, superoxide(O2•) for the first oxidation step from alcohol to aldehyde and singlet oxygen(1O2) for the second oxidation step from aldehyde to carboxylic acid, were generatedsuccessfully by electron transfer and energy transfer pathways, respectively. A range of primary and secondary alcohols were converted to thecorresponding carboxylic acids or ketones, and the optimized reaction conditionswere applied to the synthesis of benzocoumarin.
Muhammad Awais Ashraf,Shrikant D. Tambe,조은진 대한화학회 2021 Bulletin of the Korean Chemical Society Vol.42 No.4
A copper-catalyzed cascade process has been developed for the synthesis of 3-hydroxypyrrolidine derivatives in a highly diastereoselective manner. The reaction proceeded via borylative allyl copper intermediate formation from allenes; the intermediate underwent intramolecular diastereoselective cyclization followed by cascade copper-catalyzed protodeborylation, to give 3-hydroxypyrrolidines. This method could be extended to the synthesis of six-membered piperidine analogs. A series of control experiments were carried out to confirm the Cu-catalyzed facile protodeborylation of borylated homoallylic alcohols at room temperature.