Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group

被引：60

作者：

Esumi, Naoto ^{[1
]}

Suzuki, Kensuke ^{[1
]}

Nishimoto, Yoshihiro ^{[2
]}

Yasuda, Makoto ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-1 Yamadaoka, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers Ctr Op, 2-1 Yamadaoka, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 21期

关键词：

C-H FUNCTIONALIZATION; PAAL-KNORR SYNTHESIS; PHOTOREDOX CATALYSIS; (-)-MAOECRYSTAL V; GAMMA-DIKETONES; ALLYLIC ESTERS; BOND FORMATION; MAOECRYSTAL-V; EOSIN Y; ACYLATION;

D O I：

10.1021/acs.orglett.6b02869

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the visible-light-induced radical coupling reaction of silyl enol ethers with alpha-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the alpha-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, alpha-bromoketones, alpha-bromoesters, and alpha-bromoamides were applied to this system to produce the coupling compounds.

引用

页码：5704 / 5707

页数：4

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