Direct Synthesis of 1,2-Diketones
by Catalytic Aerobic Oxidative Decarboxylation of 1,3-Diketones
with Iodine and Base under Irradiation of Fluorescent
Light

Norihiro Tada; Motoki Shomura; Hiroki Nakayama; Tsuyoshi Miura; Akichika Itoh

doi:10.1055/s-0030-1258134

LETTER

Direct Synthesis of 1,2-Diketones by Catalytic Aerobic Oxidative Decarboxylation of 1,3-Diketones with Iodine and Base under Irradiation of Fluorescent Light

Norihiro Tada, Motoki Shomura, Hiroki Nakayama, Tsuyoshi Miura, Akichika Itoh*
Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
Fax: +81(58)2308108; e-Mail: itoha@gifu-pu.ac.jp;

Abstract

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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

References and Notes

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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.