58926-22-0

Upstream product

• 29179-25-7 cinnamylideneacetophenone 
• 14371-10-9 (E)-3-phenylpropenal 
• 98-86-2 acetophenone 
• 4039-82-1 Benzyl propargyl ether 
• 947692-02-6 4-benzyloxy-1-phenylbut-2-en-1-ol 
• 1497433-90-5 (E)-4-(benzyloxy)-1-phenyl-2-buten-1-yl benzoate 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 591-51-5 phenyllithium 

Downstream Products

• 7349-06-6 (1E,3E)-penta-1,3-diene-1,5-diyldibenzene 
• 3185-62-4 ((1E,3E)-5-methoxypenta-1,3-diene-1,5-diyl)dibenzene 

Relevant academic research and scientific papers

Stille couplings catalytic in tin: a "Sn-F" approach.

A new tin recycling method for Stille couplings catalytic in tin is reported. PMHS made hypercoordinate by KF((aq)) allows Me(3)SnH to be efficiently recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Relative to previously disclosed protoc

Flexible Construction of Functionalized-Pyrroles under Palladium or Copper Catalysis in the Presence of BF3 ? Et2O

We have developed a flexible approach enabling the access to highly functionalized pyrroles under palladium or copper catalysis in the presence of BF3 ? Et2O. This catalytic methodology utilizes commercially available amines as react

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.).

Stereoselective synthesis of (2 Z,4 E)-2,4-pentadien-1-ols via sequential 1,4-elimination reaction and [1,2]-wittig rearrangement starting from (E)-4-alkoxy-2-butenyl benzoates

The sequential 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1,2]-Wittig rearrangement gave (2Z,4E)-2,4-pentadien-1-ols stereoselectively. Z-Selective formation of intermediary vinyl ethers, whose stereochemistry was well elucidated by the "syn-effect", was achieved by treatment of the 2-butenyl benzoates with KOH in the presence of Pd catalyst. The subsequent [1,2]-Wittg rearrangement by use of n-BuLi proceeded with retention of the stereochemistry of the intermediary vinyl ethers.

Stille reactions catalytic in tin: A "Sn-F" route for intermolecular and intramolecular couplings

(Chemical Equation Presented) Polymethylhydrosiloxane (PMHS) made hypercoordinate by KF(aq) allows Me3SnH to be recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Starting with a variety of alkynes, in situ vinyltin formation is followed by Stille reaction with aryl, styryl, benzyl, or vinyl electrophiles present in the reaction mixture. Both inter- and intramolecular versions of the process are possible with tin loads of approximately 6 mol %. Regeneration of the organotin hydride is believed to proceed through a Me3SnF intermediate. Given the aggregated nature of organotin fluorides and the ability to use these organotins in substoichiometric quantities, the hazards and purification problems associated with the removal of organotin wastes from reaction mixtures are minimized.

Stille couplings catalytic in tin: The "Sn-O" approach

A one-pot tandem Pd-catalyzed hydrostannylation/Stille coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is most effective with Me3SnCl serving as the tin source. This protocol allows a 94% reduction of the tin requirement, while maintaining good yields (up to 90%) for a variety of Stille products. Furthermore, since one cycle requires the tin to undergo at least four transformations, each moiety of trialkyltin is experiencing a minimum of 60 reactions over the course of the hydrostannylation/Stille, sequence.

Selective conjugate alkylation of alkyllithium nucleophiles to α, β, γ, δ-unsaturated aldehydes with functionalized Lewis acid receptors

Selective 1,4- and 1,6-addition of alkyllithium reagents to α,β,γ,δ-unsaturated aldehydes has been successfully realized with fluorinated aluminum tris(2,6-diphenylphenoxide) (ATPH) derivatives as functionalized Lewis acid receptors.

Vinylogues of Bifonazole: Synthesis and Antifungal Activities

Various bifonazole-like derivatives containing styryl or arylbutadienyl groups instead of the 4-biphenylyl moiety were synthesized and tested as antifungal agents. Among the tested derivatives 11c was twice as potent as bifonazole and about 3 times more s

Equilibrium acidities of some α,ω-diphenylpolyenes

Cesium ion pair acidities were measured in THF for a series of diphenylmethane vinylogues that form α,ω-diphenylpolyenyl anions with linearly conjugated chains of 3-9 carbon atoms. The dissociation constants of the diphenylpolyenyls in THF were determined by UV-vis spectroscopy and are rationalized with an electrostatic model. Acidity and dissociation data were combined with measurements of stereoisomer equilibria to estimate the differences in delocalization energy among the diphenylpolyenyl ions. The experimental differences in acidity correlate well with AMI and molecular mechanics (MMPI) calculations.

A novel one-pot synthesis of β-hydroxy 1,3-dienes via allylic ylide-anion

A novel one-pot synthesis of β-hydroxy 1,3-dienes via allylic ylideanion with high stereoselectivity is described.