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• 111-34-2 -butyl vinyl ether 
• 59099-58-0 2-methoxyphenyl triflate 
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• 766-51-8 2-Chloroanisole 

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• 579-74-8 2-Methoxyacetophenone 

Relevant academic research and scientific papers

A robust first-pass protocol for the heck-mizoroki reaction

The Heck-Mizoroki (HM) reaction is one of the most widely used C-C bond-forming methods of contemporary synthesis. Notwithstanding this, these reactions frequently require significant optimization before efficient transformations can be obtained. We describe here the results of a study that aimed to establish a generic experimental protocol for HM reactions which enables acceptable yields from first-pass experiments. The methodology utilizes readily available stable catalysts and can be applied to a broad range of coupling partners.

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.

Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides

The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the oxidative addition of ArCl to Pd(0). Hence, an electron-rich diphosphine, 4-MeO-dppp, was introduced to facilitate the catalysis. Solvent choice is critical, however; only sluggish arylation is observed in DMF or DMSO, whereas the reaction proceeds well in ethylene glycol at 0.1-1 mol % catalyst loadings, displaying excellent regioselectivity. Mechanistic evidence supports that the arylation is turnover-limited by the oxidative addition step and, most importantly, that the oxidative addition is accelerated by ethylene glycol, most likely via hydrogen bonding to the chloride at the transition state as shown by DFT calculations. Ethylene glycol thus plays a double role in the arylation, facilitating oxidative addition and promoting the subsequent dissociation of chloride from Pd(II) to give a cationic Pd(II)-olefin species, which is key to the regioselectivity observed.

Oxygen and base-free oxidative heck reactions of arylboronic acids with olefins

A mild and efficient protocol for palladium-catalyzed oxidative Heck reactions of arylboronic acids with both electron-rich and -deficient olefins is described. In contrast to the normal oxidative Heck coupling, this new method works in the absence of a base, oxygen, or other external oxidants. With a wide variety of substrates tolerated, the method broadens the scope of palladium-catalyzed coupling reactions. Copyright

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.

α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers

Regioselective α-arylation of acyclic enol ethers by aryl trifluoromethanesulfonates, aryl bromide, aryl iodides, and aroyl chlorides is described.The outcome of the reaction proved to be dependent from the relationship between ligand and counterion in the oxidative complex.