13677-51-5

Upstream product

• 21551-47-3 4,4'-Dimethylchalcon 
• 122-00-9 para-methylacetophenone 
• 104-87-0 4-methyl-benzaldehyde 
• 106-38-7 para-bromotoluene 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 

Downstream Products

• 1421862-00-1 (E)-1,3-di-p-tolylallyl 3,5-dinitrobenzoate 
• 1421862-02-3 (E)-1,3-di-p-tolylallyl 4-nitrobenzoate 
• 1379594-82-7 (E)-3-(1,3-di-p-tolylallyl)-4-hydroxy-2H-chromen-2-one 
• 1092381-54-8 (E)-4,4′-(prop-1-ene-1,3-diyl)bis(methylbenzene) 
• 21551-47-3 4,4'-Dimethylchalcon 

Relevant academic research and scientific papers

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System

Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).

Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant

The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols

A convenient and regioselective cross-coupling of heteroaryl boronic acids with allylic alcohols under catalyst-free reaction conditions is described. The developed procedure is simple, works under external oxidant- and metal-free conditions, and proves to be very general with an unprecedented ortho-selectivity. This approach represents one of the very few examples of ortho-functionalization of boronic acids.

Mass spectrometric screening of chiral catalysts by monitoring the back reaction of quasienantiomeric products: Palladium-catalyzed allylic substitution

(Chemical Equation Presented) Back to basics: The principle of microscopic reversibility is the basis of a new screening method for chiral catalysts. Monitoring the back reaction of quasi-enantiomeric allylation products by ESIMS reveals the intrinsic enantioselectivity of palladium catalysts in allylic substitution reactions (see scheme).

Ionene-bound borohydrides: Efficient, selective, and versatile polymer-supported reducing agents

Reduction of structurally different carbonyl compounds, such as aldehydes, ketones, α,β-unsaturated enals and enones, acid chlorides, and imines was accomplished efficiently using high capacity ionene based borohydride reagents. Aldehydes and imines were reduced to the corresponding alcohols and amines in excellent yields in methanol at ambient temperature while ketones and acid chlorides were reduced in iso-propanol and THF-MeOH at reflux. Chemoselective reduction of aldehydes over ketones was achieved successfully with these reagents. Complete regioselectivity was also observed in the reduction of α,β-unsaturated aldehydes and ketones.