130925-76-7

Upstream product

• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 7393-43-3 tetraallyl tin 
• 762-73-2 trimethyl(allyl)stannane 
• 556-56-9 allyl iodid 
• 4358-87-6 (RS)-methyl mandelate 
• 106-95-6 allyl bromide 
• 1191-99-7 2,3-dihydro-2H-furan 
• 762-72-1 allyl-trimethyl-silane 
• 18854-66-5 tris(allyl)aluminum 
• 24850-33-7 allyltributylstanane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1286204-70-3 methyl 2-phenyl-2-trimethylsiloxypent-4-enoate 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 103475-86-1 (+/-)-2-hydroxy-2-phenylpent-4-enoic acid 
• 6249-80-5 1-phenylbut-3-en-1-one 

Relevant academic research and scientific papers

Stereoselective construction of quaternary carbon centers by three component coupling reactions

TiCl4 promoted coupling reactions of pyruvates with vinyl ethers such as 3,4-dihydro-2H-pyran or 2,3-dihydrofuran constructed quaternary carbon centers stereoselectively. (C) 2000 Elsevier Science Ltd.

Aryl-substituted dimethylbenzimidazolines as effective reductants of photoinduced electron transfer reactions

Photoinduced electron transfer (PET) reactions promoted by 2-aryl substituted 1,3-dimethylbenzimidazolines (Ar-DMBIH) were investigated. Excited states of Ar-DMBIH, formed by irradiation using light above 360 nm, initiate PET reductions of various organic substrates, including transformations of epoxy ketones to aldols, free radical rearrangements such as the Dowd-Beckwith ring-expansion and 5-exo hexenyl cyclization, deprotection of N-sulfonyl-indols, and allylation of acyl formates. In these processes, Ar-DMBIH possessing 1-naphthyl, 2-naphthyl, 1-pyrenyl and 9-anthryl substituents formally act as two electron and one proton donors while the hydroxynaphthyl substituted derivative serves as a two electron and two proton donor. On the basis of the results of absorption spectroscopy studies, cyclic voltammetry and DFT calculation, a mechanistic sequence for these reduction reactions is proposed that involves initial photoexcitation of the aryl chromophore of the Ar-DMBIH followed by single electron transfer (SET) to the organic substrate to generate the radical cation of benzimidazoline and the radical anion of the substrate.

Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines

A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.

Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright

Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity.

Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates

A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.

Efficient allylation of active ketones promoted by p-nitrobenzoic acid

A general and practical method of allylation of carbonyl compounds promoted by p-nitrobenzoic acid under mild reaction condition has been developed. p-Nitrobenzoic acid can be easily recovered after workup by aqueous HCl.

Allylation and crotylation of ketones and aldehydes using potassium organotrifluoroborate salts under lewis acid and montmorillonite k10 catalyzed conditions

Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF3-OEt 2 and montmorillonit

Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents

Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the react