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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

Naoto Esumi, Kensuke Suzuki, Yoshihiro Nishimoto* and Makoto Yasuda*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: nishimotochem.eng.osaka-u.ac.jp, yasudachem.eng.osaka-u.ac.jp

N. Esumi, K. Suzuki, Y. Nishimoto, M. Yasuda, Org. Lett., 2016, 18, 5704-5707.

DOI: 10.1021/acs.orglett.6b02869 (free Supporting Information)


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Abstract

A visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds provides 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst.

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Key Words

1,4-dicarbonyl compounds


ID: J54-Y2016