944344-73-4Relevant academic research and scientific papers
Carbonylative coupling of allylic acetates with aryl boronic acids
Ma, Wei,Xue, Dong,Yu, Ting,Wang, Chao,Xiao, Jianliang
supporting information, p. 8797 - 8800 (2015/05/20)
The first allylic carbonylation reaction of allylic acetates with aryl boronic acids under carbon monoxide has been developed. Using Pd-PCy3 as a catalyst, a wide spectrum of allylic acetates was carbonylated in the presence of various aryl boronic acids, affording α,β-unsaturated aryl ketones in good to excellent yields. Preliminary studies indicate that carbon monoxide always inserts at the least substituted terminal allylic carbon and the resulting β,γ-unsaturated aryl ketones generally isomerise to the ketones obtained.
Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones
Zhuo, Lian-Gang,Yao, Zhong-Ke,Yu, Zhi-Xiang
supporting information, p. 4634 - 4637 (2013/10/08)
Developing olefin isomerization reactions to reach kinetically controlled Z-alkenes is challenging because formation of trans-alkenes is thermodynamically favored under the traditional catalytic conditions using acids, bases, or transition metals as the catalysts. A new synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones to α,β-unsaturated ketones was developed, providing an easy and efficient way to access various Z-enones.
Decarboxylative allylation of glyoxylic acids with diallyl carbonate
Manjolinho, Filipe,Gruenberg, Matthias F.,Rodriguez, Nuria,Goossen, Lukas J.
supporting information; experimental part, p. 4680 - 4683 (2012/10/08)
A catalyst system consisting of Pd(PPh3)4 and P(pTol)3 was found to effectively promote the intermolecular decarboxylative coupling of α-oxocarboxylic acids with diallyl carbonate to give α,β-unsaturated ketones. The key advantage of the new reaction protocol is that preformation of the allyl esters is not required. The reaction is believed to proceed via phosphane-mediated decarboxylation of the α-oxocarboxylates, leading to acyl anion equivalents that are allylated within the coordination sphere of the palladium catalyst. Under the reaction conditions, the double bond then migrates into conjugation with the carbonyl group. Copyright
Synthesis of α,β-unsaturated ketones by Pd-catalyzed decarboxylative allylation of α-oxocarboxylates
Rodriguez, Nuria,Manjolinho, Filipe,Gruenberg, Matthias F.,Goossen, Lukas J.
, p. 13688 - 13691 (2012/01/15)
A palladium/p-tolylphosphine system has been developed that catalyzes the extrusion of carbon dioxide from α-oxocarboxylic acid allyl esters, leading to α,β-unsaturated ketones (see scheme). The palladium complex activates the substrate and mediates the carbon-carbon bond formation to give allyl ketones, and subsequent double bond shift to the α,β position. The actual decarboxylation step with formation of the acyl nucleophile is promoted by phosphine.
