70810-14-9

Upstream product

• 104-54-1 3-Phenylpropenol 
• 108-88-3 toluene 
• 37464-41-8 phenyl 3-phenyl-allyl ether 
• 16419-60-6 2-Methylphenylboronic acid 
• 95-46-5 2-methylphenyl bromide 
• 34862-91-4 1-phenyl-3-(o-tolyl)prop-2-en-1-ol 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 

Downstream Products

• 1431318-03-4 3-benzyl-5-methyl-1,2-diphenylnaphthalene 
• 78987-21-0 N-(2-methylphenyl)-3-phenylacrylamide 
• 1352733-12-0 (E)-5-styryl-1-(o-tolyl)-1Htetrazole 
• 1352733-28-8 (E)-5-(2-methylstyryl)-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: The allylation of aryl halides with allylic alcohols

Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.

In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids

A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).

Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes

A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.

FeCl3·6H2O-catalyzed selective reduction of allylic halides to alkenes with concomitant oxidation of benzylic alcohols to aldehydes

Iron-catalyzed direct reduction of allylic halides with benzylic alcohol was achieved, providing a new, simple, and efficient method for conducting highly regioselective hydrodehalogenation. This method not only features a readily available reductant, an

Pd-catalyzed π-chelation assisted ortho-C-H activation and annulation of allylarenes with internal alkynes

The synthesis of highly substituted naphthalenes from allylarenes and alkynes is described. This reaction proceeds via π-coordination of an allylic carbon-carbon double bond to the Pd(II) center and is followed by ortho selective C-H bond activation.

Palladium-catalyzed allylic arylation of allylic ethers with arylboronic acids using hydrazone ligands

Unsymmetrical 1,3-diarylpropenes were synthesized in good to high yields by the palladium-catalyzed allylic arylation of allylic ethers, such as a cinnamyl phenyl ether, with a variety of arylboronic acids using a hydrazone 1a-Pd(OAc)2 system in DMAc/H2O. Using this catalyst, eugenol was also synthesized from allyl phenyl ether with (4-hydroxy-3- methoxyphenyl)boronic acid pinacol ester. A palladium-catalyzed allylic arylation of cinnamyl phenyl ether derivatives with a variety of arylboronic acids using 5 mol-% of a hydrazone 1a-Pd(OAc)2 system in DMAc/H 2O at 50 °C gave 1,3-diarylpropenes in good yields. We also succeeded with the synthesis of eugenol by a palladium-catalyzed allylic arylation. Copyright

FeCl3 · 6H2O catalyzed disproportionation of allylic alcohols and selective allylic reduction of allylic alcohols and their derivatives with benzyl alcohol

Iron chloride has been found to be an efficient catalyst for the disproportionation of allylic alcohols, which provides a convenient method for selective transformation of allylic alcohols to alkenes and α,β- unsaturated ketones. Furthermore, this catalytic system is also effective for highly selective allylic reduction of allylic alcohols, allylic ethers, and allylic acetates with benzyl alcohol under neutral and convenient reaction conditions.

Chlorine borrowing: An efficient method for an easier use of alcohols as alkylation agents

Chlorine functionalised tin dioxide nanoparticles proved able to partially convert alcohols into the corresponding chlorides, which act as alkylation agents with an increased electrophilicity, as evidenced on ether formation and Friedel-Crafts reactions.

Gas-Phase Diels-Alder Reaction of the o-Quinodimethane Radical Cation and Neutral Styrene

The collision complex formed in the ion-molecule reaction of o-quinodimethane radical cation and neutral styrene was investigated by using mass spectrometry/mass spectrometry (MS/MS) techniques.The reaction was conducted in a high-pressure chemical-ionization source, where the reagents were ionized by low-energy charge exchange and the reaction products were collisionally stabilized.The collision complex was shown to have the structure of 2-phenyltetralin through the use of deuterium labeling and direct comparison with the properties of reference radical cations.These results establish the structural integrity of low-energy o-quinodimethane radical ions and are evidence for a Diels-Alder reaction mechanism.