489434-12-0

Upstream product

• 111-34-2 -butyl vinyl ether 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 1126-46-1 Methyl 4-chlorobenzoate 

Downstream Products

• 3609-53-8 methyl 4-acetylbenzoate 

Relevant academic research and scientific papers

Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers

The combination of Pd(OAc)2 with 1,3-bis(diphenylphosphino) propane (dppp) in ethylene glycol constitutes a high-performance catalytic system for highly regioselective arylation of a range of electron-rich vinyl ethers by aryl bromides to provide, upon hydrolysis, alkyl aryl ketones and cyclic ketals in good yields with up to 3.75 × 105 TON and 15625 h-1 TOF.

The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors

No salt please: Halide scavengers AgOTf and TlOAc are not required for the Heck coupling of electron-rich olefins with aryl bromides and chlorides. Using ammonium additives, these reactions can be carried out in either an imidazolium ionic liquid or a common molecular solvent, thus furnishing 1,1′- disubstituted olefins in high yields with excellent regioselectivities. (Chemical Equation Presented).

Synthesis of functionalised acetophenone

Nickel catalysed Heck arylation of the electron-rich olefin n-butyl vinyl ether with a wide variety of aryl bromides has been accomplished in the ionic liquid [bmim][BF4], affording an efficient green chemistry synthetic procedure for preparing functionalised acetophenone. The reaction gave a high regioselectivity and high yield without the need for the costely or toxic halide scavengers, leading predominantly to a branch-arylated α-product.

Ionic liquid-promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides

Palladium-catalyzed regioselective Heck arylation of the electron-rich olefins, vinyl ethers 1a-d, enamides 1e-g, and allyltrimethylsilane 1h, has been accomplished in imidazolium ionic liquids with a wide range of aryl bromides and iodides instead of the commonly used, but commercially unavailable and expensive, aryl triflates. The reaction proceeded with high efficiency and remarkable regioselectivity without the need for costly or toxic halide scavengers, leading exclusively to substitution by aryl groups of diverse electronic and steric properties at the olefinic carbon α to the heteroatom of 1a-g and β to the heteroatom of 1h. In contrast, the arylation reaction in molecular solvents led to mixtures of regioisomers under similar conditions. Several lines of evidence point to the unique regiocontrol stemming from the ionic environment provided by the ionic liquid that alters the reaction pathway. The chemistry provides a simple, effective method for preparing branched, arylated olefins and contributes to the extension of Heck reaction to a wider range of substrates.

Palladium-catalyzed regioselective arylation of an electron-rich olefin by aryl halides in ionic liquids

equation presented Palladium-catalyzed arylation of the electron-rich olefin butyl vinyl ether has been accomplished in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]), using as the arylating agents aryl iodides and bromides instead of the commonly used, but commercially unavailable and expensive, aryl triflates. The reaction proceeds with high efficiency and remarkable regioselectivity, leading almost exclusively to substitution by various aryl groups at the olefinic carbon α to the heteroatom of butyl vinyl ether.

1,10-Phenanthroline Derivatives: A New Ligand Class in the Heck Reaction. Mechanistic Aspects

Mechanistic studies concerning the use of 1,10-phenanthroline derivatives as palladium ligands in the Heck reaction are described.The work is focused on the steering factors for the coordination of unsaturated systems onto palladium(0) and palladium(II) complexes.