65693-16-5Relevant articles and documents
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
[(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.
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.
