93433-84-2

Upstream product

• 150-76-5 4-methoxy-phenol 
• 4392-24-9 Cinnamyl bromide 
• 104-54-1 3-Phenylpropenol 
• 100-52-7 benzaldehyde 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 2687-12-9 cinnamyl chloride 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 38276-84-5 2-(α-Phenyl-allyl)-4-methoxy-phenol 
• 134539-86-9 1-methyl-4-(3-phenyl-2-propen-1-yl)benzene 
• 139139-75-6 4-methoxy-4-(3-phenyl-prop-2-enyloxy)-2,5-cyclohexanedione 

Relevant academic research and scientific papers

Pd-catalyzed substitution of the oh group of nonderivatized allylic alcohols by phenols

Nonactivated phenols have been employed as nucleophiles in the allylation of nonderivatized allylic alcohols to generate allylated phenolic ethers with water as the only byproduct. A Pd[BiPhePhos] catalyst was found to be reactive to give the O-allylated phenols in good to excellent yields in the presence of molecular sieves. The reactions are chemoselective in which the kinetically favored O-allylated products are formed exclusively over the thermodynamically favored C-allylated products.

Halogen Bond Catalyzed Bromocarbocyclization

A halogen bond catalyzed bromo-carbocyclization of N-cinnamyl sulfonamides and O-cinnamyl phenyl ethers has been developed. N-methyl 4-iodopyridinium triflate is used as the halogen-bonding organocatalyst and the reaction is highly chemoselective. This report represents the first proof-of-concept for halogen-bonding organocatalyst-promoted electrophilic halogenation. Mechanistic study suggests the autocatalytic nature of this reaction.

From precursor to catalyst: The involvement of [Ru(η5- Cp*)Cl2]2 in highly branch selective allylic etherification of cinnamyl chlorides

(RuCp*Cl2)2, a general entry into Cp*Ru sandwich and half-sandwich chemistry was first used as a precatalyst in allylic etherification of cinnamyl chlorides with up to 98:2 regioselectivity (19 examples). Both the solvent effect and the exsiccant reaction condition are crucial to the reactivity and selectivity. Preliminary mechanism studies and the demonstration of Fluoxetine synthesis were presented in this work as well.

Regio- and enantioselective allylic substitution with less active N- or O-nucleophiles catalyzed by iridium-complex of bis(oxazolinyl)pyridine

The utility of hydroxylamines as nitrogen nucleophiles was investigated in the iridium-catalyzed regio- and enantioselective allylic substitution. Allylic substitution with hydroxylamines proceeded with good enantioselectivities by using the iridium-complex of bis(oxazolinyl)pyridine ligand. The good regio- and enantioselectivities were also achieved in the reaction with alkylamines, p-anisidine, and 4-methoxyphenol.

New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions

New tetraimidazolinium and tetrabenzimidazolium salts have been prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce new ruthenium catalysts that

Ruthenium(IV) complexes featuring p,O-chelating ligands: Regioselective substitution directly from allylic alcohols

(Figure Presented) Branching out: A new ruthenium(IV) complex (1), containing a P,O-chelating ligand, is an efficient precatalyst for regioselective allylations starting from various allylic alcohol derivatives.

Regioselective iron-catalyzed decarboxylative allylic etherification

[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.