Selective Debromination and alpha-Hydroxylation of alpha-Bromo Ketones Using Hantzsch Esters as Photoreductants
- 주제(키워드) debromination , Hantzsch esters , hydroxylation , photoreductants
- 관리정보기술 faculty
- 등재 SCIE, SCOPUS
- 발행기관 WILEY-V C H VERLAG GMBH
- 발행년도 2016
- URI http://www.dcollection.net/handler/ewha/000000125675
- 본문언어 영어
- Published As http://dx.doi.org/10.1002/adsc.201500734
초록/요약
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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