94739-52-3Relevant academic research and scientific papers
Regioselective Isomerization of 2,3-Disubstituted Epoxides to Ketones: An Alternative to the Wacker Oxidation of Internal Alkenes
Lamb, Jessica R.,Mulzer, Michael,Lapointe, Anne M.,Coates, Geoffrey W.
, p. 15049 - 15054 (2015/12/08)
We report an alternative pathway to the Wacker oxidation of internal olefins involving epoxidation of trans-alkenes followed by a mild and highly regioselective isomerization to give the major ketone isomers in 66-98% yield. Preliminary kinetics and isotope labeling studies suggest epoxide ring opening as the turnover limiting step in our proposed mechanism. A similar catalytic system was applied to the kinetic resolution of select trans-epoxides to give synthetically useful selectivity factors of 17-23 for benzyl-substituted substrates.
Palladium-catalyzed mono-α-arylation of carbonyl-containing compounds with aryl halides using dalphos ligands
Crawford, Sarah M.,Alsabeh, Pamela G.,Stradiotto, Mark
, p. 6042 - 6050,9 (2020/09/02)
We report the extension and optimization of the [Pd(cinnamyl)Cl] 2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides. Aryl methyl ketones, heteroaryl methyl ketones, propiophenones, malonates, and methoxyacetone can be α-arylated under relatively mild conditions and in good yields. We also report the limitations of the ligand/catalyst system towards other classes of carbonyl-containing compounds. We report the application of the [Pd(cinnamyl)Cl]2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides.
Electroreductive Acylation of Benzyl Chlorides with Acid Anhydrides. Stereoselective Formation of (E)-Enol Esters from Benzyl Alkyl Ketones
Nishiguchi, Ikuzo,Oki, Tsuneo,Hirashima, Tsuneaki,Shiokawa, Jiro
, p. 2005 - 2008 (2007/10/02)
Electroreduction of benzyl chlorides in the presence of acid anhydrides brought about stereoselective formation of (E)-enol esters of the corresponding benzyl alkyl ketones, the initial acylated products, in good to moderate yields.
