39755-14-1Relevant articles and documents
Nickel-catalyzed organozinc-promoted carbocyclizations of electron-deficient alkenes with tethered unsaturation
Montgomery, John,Oblinger, Eric,Savchenko, Alexey V.
, p. 4911 - 4920 (1997)
A nickel-catalyzed method for cyclizations of electron- deficient alkenes with tethered unsaturation in the presence of organozincs was developed. Considerable flexibility in the structure of each reactive component was observed, Enones, alkylidene malonates, unsaturated β-ketoesters, and nitroalkenes participated as the electrondeficient alkene; alkynes, enones, 1,3- dienes, and aldehydes participated as the tethered unsaturation; and a variety of sp2 and sp3-hybridized organozincs, including those that possess β-hydrogens, participated as the nucleophilic component. Substrate structure, organozinc structure, and ligand structure all played a significant role in determining product selectivities. Of particular synthetic significance was the opportunity to prepare either E or Z tri- or tetrasubstituted alkenes from a common alkyne. A discussion of probable mechanisms is provided.
Visible-light-promoted site-specific and diverse functionalization of a c(sp3)-c(sp3) bond adjacent to an arene
Fang, Fang,Liu, Zhong-Quan,Sun, Minzhi,Wang, Nengyong,Wang, Yaxin,You, Huichao,Zhao, Jianyou
, p. 6603 - 6612 (2020/07/27)
We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.
TEMPO-catalyzed aerobic oxygenation and nitrogenation of olefins via C=C double-bond cleavage
Wang, Teng,Jiao, Ning
, p. 11692 - 11695 (2013/09/02)
A novel TEMPO-catalyzed aerobic oxygenation and nitrogenation of hydrocarbons via C=C double-bond cleavage has been disclosed. The reaction employs molecular oxygen as the terminal oxidant and oxygen-atom source by metal-free catalysis under mild conditions. This method can be used for the preparation of industrially and pharmaceutically important N- and O-containing motifs, directly from simple and readily available hydrocarbons.