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Selective Debromination and α‐Hydroxylation of α‐Bromo Ketones Using Hantzsch Esters as Photoreductants
Author(s) -
Jung Jaehun,
Kim Jun,
Park Gyurim,
You Youngmin,
Cho Eun Jin
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500734
Subject(s) - chemistry , hydroxylation , solvent , molecular oxygen , ketone , organic chemistry , oxygen , electron transfer , photoinduced electron transfer , photochemistry , enzyme
Two transformations initiated by photoinduced one‐electron transfer to α‐bromo ketones have been demonstrated. Hantzsch esters donate one electron to α‐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 α‐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.