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Selective Debromination and alpha-Hydroxylation of alpha-Bromo Ketones Using Hantzsch Esters as Photoreductants
- Selective Debromination and alpha-Hydroxylation of alpha-Bromo Ketones Using Hantzsch Esters as Photoreductants
- Jung, Jaehun; Kim, Jun; Park, Gyurim; You, Youngmin; Cho, Eun Jin
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- 1615-4150; 1615-4169
- vol. 358, no. 1, pp. 74 - 80
- debromination; Hantzsch esters; hydroxylation; photoreductants
- WILEY-V C H VERLAG GMBH
- SCI; SCIE; SCOPUS
- Two transformations initiated by photoinduced one-electron transfer to a-bromo ketones have been demonstrated. Hantzsch esters donate one electron to alpha-bromo ketones under photoirradiation, promoting reductive debromination. Subsequent reactions of the resulting radical species of the ketones with molecular oxygen and Hantzsch esters lead to alpha-hydroxylation or debromination, respectively. The relative dominance of the two pathways depends profoundly on the reaction conditions, including solvent, O-2 levels, and the concentration of the Hantzsch esters. The synthetic protocols feature advantages because they require the environmentally benign sources, molecular oxygen and visible light.
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