1147357-09-2

Upstream product

• 19957-01-8 1-p-Tolyl-3-(4-chlorphenyl)-propen-⁽¹⁾-ol-⁽³⁾ 
• 105643-15-0 4-chlorocinnamyl acetate 
• 5142-75-6 tri(p-tolyl)bismuth 
• 99-91-2 para-chloroacetophenone 
• 122-00-9 para-methylacetophenone 
• 166823-95-6 (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-ol 
• 166824-02-8 (E)-1-(4-chlorophenyl)-3-(p-tolyl)prop-2-en-1-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 19672-63-0 1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 
• 106-43-4 para-chlorotoluene 
• 60691-90-9 3-bromo-1-(p-chlorophenyl)-1-propene 
• 104-88-1 4-chlorobenzaldehyde 
• 106-38-7 para-bromotoluene 
• 19672-63-0 (2E)-1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Direct deoxygenation of active allylic alcohols via metal-free catalysis

Direct metal-free deoxygenation of highly active allylic alcohols catalyzed by a Br?nsted acid was achieved, which avoids tedious reaction steps and eliminates metal contamination. By examining a series of Br?nsted acids, alcohols, reaction temperatures and so on, up to 94% yield was obtained with 10 mol% TsOH·H2O as the catalyst and 2 equiv. of p-methylbenzyl alcohol as the reductant at 80 °C for 2 h. The system was mainly suitable for aromatic allylic alcohols, and the yield was excellent as determined via gram-scale synthesis. The main product was double bond near the side of a more electron-rich aryl group when allylic alcohols featuring different substituents at the 1 and 3 positions were used as the substrates. Deuterium-labelled experiments clearly demonstrated that the hydrogen source was the methylene of p-methylbenzyl alcohol and other control experiments indicated the existence of two ether intermediates. Interestingly, in situ hydrogen transfer of allylic benzyl ether is a key process, but kinetic isotopic effect studies (kH/kD = 1.28) showed that the C-H bond cleavage was not the rate-determining step. A possible mechanism involving carbocations, ether intermediates and hydrogen transfer is proposed.

Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

Allylic activation across an Ir-Sn heterobimetallic catalyst: Nucleophilic substitution and disproportionation of allylic alcohol

A nucleophilic substitution of allylic alcohols with carbon (arene, heteroarene, allyltrimethylsilane, and 1,3-dicarbonyl compound), sulfur (thiol), oxygen (alcohol), and nitrogen (sulfonamide) nucleophiles has been demonstrated using an in house developed [Ir(COD)(SnCl3)l(μ-Cl)]2 heterobimetallic catalyst in 1,2-dichloroethane to afford the corresponding allylic products in moderate to excellent yields. In 4-hydroxycoumarin, allylation occurs at the 3-position. The diaryl-substituted allylic alcohols undergo disproportionation in presence of the heterobimetallic catalyst to provide the corresponding alkenes and chalcones. An electrophilic mechanism is proposed from Hammett correlation study.

Arylations of allylic acetates with triarylbismuths as atom-efficient multi-coupling reagents under palladium catalysis

Arylation of allylic acetates employing triarylbismuths as multi-coupling reagents under palladium-catalyzed conditions was reported. Triarylbismuths as nucleophilic coupling partners were used in sub-stoichiometric amounts with respect to allylic acetate

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.