Selective Debromination and alpha-Hydroxylation of alpha-Bromo Ketones Using Hantzsch Esters as Photoreductants
- Authors
- Jung, Jaehun; Kim, Jun; Park, Gyurim; You, Youngmin; Cho, Eun Jin
- Issue Date
- Jan-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- debromination; Hantzsch esters; hydroxylation; photoreductants
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.358, no.1, pp 74 - 80
- Pages
- 7
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 358
- Number
- 1
- Start Page
- 74
- End Page
- 80
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/7379
- DOI
- 10.1002/adsc.201500734
- ISSN
- 1615-4150
1615-4169
- Abstract
- 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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Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
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