65693-16-5Relevant academic research and scientific papers
Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative heck reactions of arylboronic acids or alkenylboronate with allyl esters
Su, Yijin,Jiao, Ning
supporting information; experimental part, p. 2980 - 2983 (2009/12/05)
A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. β-H elimination is highly chemoselectively controlled, leading to γ-substituted allyl esters, which is contrary to the traditional
Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group
Pan, Delin,Chen, Anjun,Su, Yijin,Zhou, Wang,Li, Si,Jia, Wei,Xiao, Juan,Liu, Qingjian,Zhang, Liangren,Jiao, Ning
supporting information; experimental part, p. 4729 - 4732 (2009/02/06)
(Chemical Equation Presented) What leaving group? Organic halides and allylic esters undergo efficient Pd-catalyzed Heck reactions under mild conditions in air to form a new C-C bond without elimination of the β-OAc group in the intermediate palladium complex. Instead a highly regioselective β-H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme).
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
Chiral ligands and their transition metal complexes
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, (2008/06/13)
The present invention relates to chiral phosphorus compounds and their transition metal complexes, and also to the use of these transition metal complexes, especially in asymmetric syntheses.
One-pot synthesis of γ,δ-unsaturated carbonyl compounds from allyl alcohols and vinyl or isopropenyl acetates catalyzed by [IrCl(cod)] 2
Morita, Masao,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 6285 - 6286 (2007/10/03)
One-pot synthesis of γ,δ-unsaturated carbonyl compounds from allyl alcohols and vinyl or isopropenyl acetates was achieved through in situ generation of allyl vinyl ethers by the action of the [IrCl(cod)]2 complex followed by Claisen rearrangement of the resulting ethers. For instance, the reaction of trans-2-methyl-3-phenyl-2-propen-1-ol with isopropenyl acetate in the presence of [IrCl(cod)]2 (1 mol %) and Cs2CO 3 (5 mol %) at 100 °C for 3 h followed by 140 °C for 15 h afforded 5-methyl-4-phenyl-5-hexen-2-one in 72% yield. When vinyl acetate was employed in place of isopropenyl acetate, 4-methyl-3-phenyl-4-pentenal was obtained in 83% yield.
Oxidation by Cobalt(III) Acetate. Part 8. Effects of Substituents on Product Distributions in Oxidation of Aromatic Olefins by Cobalt(III) Acetate
Morimoto, Takashi,Hirano, Masao,Koyama, Tsuyoshi
, p. 1109 - 1116 (2007/10/02)
Oxidation of aromatic olefins by cobalt(III) acetate in acetic acid under nitrogen gave both allylic acetates and glycol monoacetates.Disubstituted olefins were oxidized by the oxidant to give predominantly allylic acetates.Glycol monoacetates were minor products except for the case of 1-phenylisobutene which was slowly oxidized to give the corresponding glycol monoacetate.In the oxidation of tri- and tetra-substituted olefins, the yield of glycol monoacetate increased at the expense of that of allylic acetate.A mechanism, in which the reaction proceeds through a Co-co-ordinated radical kation formed by an one-electron abstraction from olefin by cobalt(III) acetate, is suggested.
