121236-20-2Relevant academic research and scientific papers
Facile Synthesis of γ-Ketonitriles in Water via C(sp2)–H Activation of Aromatic Aldehydes over Cu?g-C3N4 under Visible-Light
Bhardiya, Smita R.,Rai, Ankita,Rai, Vijai K.,Sheshma, Harendra,Singh, Manorama,Verma, Fooleswar
, p. 5841 - 5846 (2020)
A facile C(sp2)–H activation of aldehyde under visible-light conditions using Cu?g-C3N4 as photocatalyst and water as solvent is reported. The envisaged method involves photocatalytic intermolecular Stetter reaction using
Copper(i)-catalyzed ring-opening cyanation of cyclopropanols
Feng, Yi-Si,Shu, Yong-Jin,Cao, Ping,Xu, Tao,Xu, Hua-Jian
, p. 3590 - 3593 (2017)
A copper(i)-catalyzed ring-opening cyanation of cyclopropanols was developed. The reaction provides an alternative method to achieve β-cyano ketones efficiently. This reaction exhibits good functional group compatibility under mild conditions and can be scaled up to the gram scale. Preliminary mechanistic studies suggest that the reaction might go through a free radical process.
2-CYANOETHYLZINC IODIDE: A NEW REAGENT WITH REACTIVITY UMPOLUNG
Yeh, Ming Chang P.,Knochel, Paul
, p. 2395 - 2396 (1988)
2-Cyanoethylzinc iodide 1 generated in over 90percent yield from 3-iodopropionitrile and zinc in THF can be transmetallated to the copper and titanium derivatives 3 and 4 which react in good yields, respectively, with acyl chlorides, enones, allylic halides and benzaldehyde.
Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: Applications and mechanism thereof
Balletti, Matteo,De Pedro Beato, Eduardo,Mazzarella, Daniele,Melchiorre, Paolo
, p. 6312 - 6324 (2020/08/24)
We detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue LEDs) to activate acyl and carbamoyl radical precursors, which, due to their high reduction potential, are not readily prone to redox-based activation mechanisms. To elucidate the key mechanistic aspects of this catalytic photochemical radical generation strategy, we used a combination of transient absorption spectroscopy investigations, electrochemical studies, quantum yield measurements, and the characterization of key intermediates. We identified a variety of off-the-cycle intermediates that engage in a light-regulated equilibrium with reactive radicals. These regulated equilibriums cooperate to control the overall concentrations of the radicals, contributing to the efficiency of the overall catalytic process and facilitating the turnover of the catalyst. This journal is
Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis
Cartier, Alex,Levernier, Etienne,Corcé, Vincent,Fukuyama, Takahide,Dhimane, Anne-Lise,Ollivier, Cyril,Ryu, Ilhyong,Fensterbank, Louis
supporting information, p. 1789 - 1793 (2019/01/09)
Primary, secondary, and tertiary alkyl radicals formed by the photocatalyzed oxidation of organosilicates underwent efficient carbonylation with carbon monoxide (CO) to give a variety of unsymmetrical ketones. This study introduces the possibility of radi
Direct Aldehyde Csp2?H Functionalization through Visible-Light-Mediated Photoredox Catalysis
Vu, Minh Duy,Das, Mrinmoy,Liu, Xue-Wei
supporting information, p. 15899 - 15902 (2017/11/15)
The development of methods for carbon–carbon bond formation under benign conditions is an ongoing challenge for synthetic chemists. In recent years there has been considerable interest in using selective C?H activation as a direct route for generating rea
Process for producing an omega-functionalized aliphatic carboxylic acid and intermediate products of said process, including 2-oxepanone-7-substituted products
-
, (2008/06/13)
A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized α-olefins or acrylic esters. The process comprises an addition step, an oxidation step, an isomerization step, and one or more hydrogenation steps. The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products, including 2-oxepanone-7-substituted products.
Double Alkylation of Carbon Monoxide via Free Radicals: Synthesis of Unsymmetrical Ketones
Ryu, Ilhyong,Kusano, Kazuya,Yamazaki, Hiroshi,Sonoda, Noboru
, p. 5003 - 5005 (2007/10/02)
A novel method for the synthesis of unsymmetrical ketones via the free radical carbonylation of alkyl halides is described.The mechanism of the reaction involves the trapping of an alkyl free radical by CO, the addition of the acyl free radical so formed to an alkene, and termination of the reaction by the abstraction of a hydrogen atom from tributyltin hydride by the product acyl-substituted free radical.
