37464-41-8

Upstream product

• 139-02-6 sodium phenoxide 
• 4392-24-9 Cinnamyl bromide 
• 108-95-2 phenol 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 104-54-1 3-Phenylpropenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 2687-12-9 cinnamyl chloride 
• 403825-39-8 1-chloro-4-(1-phenoxyallyl)benzene 
• 512789-26-3 1-methyl-4-((1-phenylallyl) oxy) benzene 
• 138621-80-4 1-phenyl-1-phenoxy-2-propene 
• 1200591-26-9 C₁₆H₁₄O₃ 
• 86537-61-3 ethyl cinnamylcarbonate 
• 85217-69-2 cinnamyl methyl carbonate 
• 1746-13-0 allyl phenyl ether 

Downstream Products

• 64806-63-9 3-phenoxypropylbenzene 
• 38276-75-4 2-(1-phenylallyl)phenol 
• 23431-45-0 5-Phenyl-hept-6-en-1-ol 
• 2243-53-0 styrylacetic acid 
• 59192-95-9 4-(trans-2-phenylcyclopropyl)morpholine 
• 116043-57-3 1-phenoxy-3-phenyl-1Z-hepten-4-ol 
• 60835-95-2 1-phenyl-1,4-nonadiene 
• 134539-86-9 1-methyl-4-(3-phenyl-2-propen-1-yl)benzene 
• 35856-80-5 4-(3-phenylallyl)anisole 
• 6948-68-1 1-chloro-4-(3-phenyl-2-propen-1-yl)benzene 
• 24126-82-7 4-(3-phenyl-2-propen-1-yl)phenol 
• 260782-78-3 4-(3-phenyl-2-propen-1-yl)-1-(trifluoromethyl)benzene 
• 62056-35-3 4-(3-phenyl-1-propen-1-yl)-1-(trifluoromethyl)benzene 
• 70810-16-1 1-methyl-3-(3-phenyl-2-propen-1-yl)benzene 

Relevant academic research and scientific papers

Enantio- And regioselective asymmetric allylic substitution using a chiral aminophosphinite ruthenium complex: an experimental and theoretical investigation

The design and synthesis of a new chiral aminophosphinite-ligated ruthenium complex is described. The ruthenium complex, [Ru(AMP)2(CH3CN)2][BPh4]2{AMP = (S)-tert-butyl 1-(diphenylphosphinooxy)-3-methylbutan-2-ylcarbamate}, has been found to catalyze nucleophilic addition of phenol and carboxylic acid to allyl chloride in a highly regioselective fashion with enantiomeric excess ranging from 12 to 90.

Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation

Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl rad

Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex

A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.

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.

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.

Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph2SRfn][OTf] with alkenes is described. The reaction of [Ph2SRfn][OTf] (Rfn = CF3, CH2CF3) with alkenes in the presence of 10 mol% Pd[P(t-Bu)3]2 and TsOH at room temperature provided the corresponding phenylation products in good to high yields. The bases that benefit the traditional Mizoroki-Heck reactions severely inhibited the transformation with [Ph2SRfn][OTf], whereas acids significantly improved the reaction. This protocol supplies a new class of cross-coupling partners for Mizoroki-Heck-type reactions and gains important insights into the reactivity of phenylsulfonium salts either with or without fluorine-containing alkyl groups as the promising phenylation reagents in organic synthesis.

Oxidative cleavage of allyl ethers by an oxoammonium salt

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

Oxidative cyclization of alkenoic acids promoted by AgOAc

Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.

Origins of Regioselectivity in Iridium Catalyzed Allylic Substitution

Detailed studies on the origin of the regioselectivity for formation of branched products over linear products have been conducted with complexes containing the achiral triphenylphosphite ligand. The combination of iridium and P(OPh)3 was the first catalytic system shown to give high regioselectivity for the branched product with iridium and among the most selective for forming branched products among any combination of metal and ligand. We have shown the active catalyst to be generated from [Ir(COD)Cl]2 and P(OPh)3 by cyclometalation of the phenyl group on the ligand and have shown such species to be the resting state of the catalyst. A series of allyliridium complexes ligated by the resulting P,C ligand have been generated and shown to be competent intermediates in the catalytic system. We have assessed the potential impact of charge, metal-iridium bond length, and stability of terminal vs internal alkenes generated by attack at the branched and terminal positions of the allyl ligand, respectively. These factors do not distinguish the regioselectivity for attack on allyliridium complexes from that for attack on allylpalladium complexes. Instead, detailed computational studies suggest that a series of weak, attractive, noncovalent interactions, including interactions of H-bond acceptors with a vinyl C - H bond of the alkene ligand, favor formation of the branched product with the iridium catalyst. This conclusion underscores the importance of considering attractive interactions, as well as repulsive steric interactions, when seeking to rationalize selectivities.

Regio- and Enantioselective Allylation of Phenols via Decarboxylative Allylic Etherification of Allyl Aryl Carbonates Catalyzed by (Cyclopentadienyl)ruthenium(II) Complexes and Pyridine-Hydrazone Ligands

(Cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate [CpRu(CH3CN)3][PF6] in combination with pyridine-hydrazone ligands efficiently catalyzes the asymmetric decarboxylative allylic rearrangement of allyl aryl carbonates. Formation of C-O bonds with high regio- and enantioselectivity ratios (up to 95:5 and 98% ee) is obtained. Good stereocontrol of the pseudotetrahedral geometry of the CpRu moiety is achieved by the hydrazone ligand and its "electron-poor" nature is evidenced through the epimerization of the hexacoordinated TRISPHAT-N anion.