149764-53-4Relevant academic research and scientific papers
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
Esumi, Naoto,Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto
supporting information, p. 5704 - 5707 (2016/11/17)
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.
Catalytic Effect of Five-Coordinate Organotin Bromide or Tetraphenylstibonium Bromide on the Chemo- and Stereoselective Addition of Tin Enolate to α-Halo Ketone
Yasuda, Makoto,Oh-hata, Tatsuhiro,Shibata, Ikuya,Baba, Akio,Matsuda, Haruo,Sonoda, Noboru
, p. 1180 - 1186 (2007/10/02)
Two types of catalysts, five-coordinate organotin bromides and tetraphenylstibonium bromide, similarly promoted the selective addition of tin enolates to the carbonyl moiety in α-halo ketones.The reaction with 2-chlorocyclohexanones and the enolates gave
SYNTHESIS OF 1,4-DIKETONES, 3,4-EPOXY KETONES, AND 2,4-DISUBSTITUTED FURANS BASED ON THE PRODUCTS FROM CONDENSATION OF THE MAGNESIUM ENOLATES OF KETONES WITH α-BROMO KETONES
Kel'in, A. V.,Kulinkovich, O. G.
, p. 202 - 206 (2007/10/02)
4-Bromo-3-hydroxy ketones were obtained by the condensation of methyl ketones with 2-bromo ketones in the presence of tert-butoxymagnesium bromide or by the action of organomagnesium compounds on 2-bromo ketones.The reaction of 4-bromo-3-hydroxy ketones w
Facile Control of Regioselectivity in the Reaction of Tin Enolates with α-Halogeno Carbonyls by Additives
Yasuda, Makoto,Oh-hata, Tatsuhiro,Shibata, Ikuya,Baba, Akio,Matsuda, Haruo
, p. 859 - 866 (2007/10/02)
Tin enolates 1 reacted with α-halogeno ketones 2 and esters 10 to give a variety of 1,4-diketones 3 and γ-keto esters 11, respectively, in the presence of appropriate additives such as hexamethylphosphoric triamide (HMPT), tributylphosphine oxide and tetrabutylammonium bromide, while complexation of these additives with tributyltin bromide allowed catalytic production of β-keto oxiranes 4 instead of 3.The reaction mechanism for the preparation of 1,4-diketone 3 is discussed.
