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DOI: 10.1055/s-0030-1258134
Direct Synthesis of 1,2-Diketones by Catalytic Aerobic Oxidative Decarboxylation of 1,3-Diketones with Iodine and Base under Irradiation of Fluorescent Light
Publication History
Publication Date:
09 July 2010 (online)
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Abstract
We report a catalytic direct synthesis of 1,2-diketone from 1,3-diketone through iodine/base-catalyzed aerobic photooxidation under visible-light irradiation of fluorescent lamp.
Key words
photooxidation - iodine - aerobic - 1,3-diketone - 1,2-diketone
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References and Notes
Typical Procedure
A
solution of dibenzoylmethane (1a, 0.3 mmol),
I2 (0.003 mmol), and Ca(OH)2 (0.15 mmol) in
dry EtOAc (5 mL) in a Pyrex test tube, purged with an O2 balloon,
was stirred and irradiated externally with four of 22 W fluorescent
lamps for 10 h. The reaction mixture was concentrated under reduced pressure.
The pure product 2a was obtained by preparative TLC.
Iodide 5, which is provided by alternative method, is converted into 2a in 66% yield under our standard conditions in the absence of I2.