title: 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.
abstract: We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-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 α-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, α-bromoketones, α-bromoesters, and α-bromoamides were applied to this system to produce the coupling compounds.
authors: Department of Applied Chemistry and ‡Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University , 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors: Naoto
authors: N
authors: Esumi
authors: Department of Applied Chemistry and ‡Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University , 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors: Kensuke
authors: K
authors: Suzuki
authors: Department of Applied Chemistry and ‡Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University , 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors: Yoshihiro
authors: Y
authors: Nishimoto
authors: Department of Applied Chemistry and ‡Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University , 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors: Makoto
authors: M
authors: Yasuda