3708-35-8

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 105-53-3 diethyl malonate 
• 36195-56-9 (E)-but-2-en-1-yl phenyl sulfide 
• 5848-60-2 (E)-1-phenyl-3-(phenylthio)propene 
• 16215-11-5 trans-cinnamyl p-tolyl sulfone 
• 69562-10-3 1-phenyl-3-phenylseleno-1-propene 
• 103-54-8 cinnamyl acetate 
• 85217-69-2 cinnamyl methyl carbonate 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 2687-12-9 cinnamyl chloride 
• 66684-75-1 diethyl 2-[3-phenylprop-2-en-1-ylidene]propanedioate 
• 34727-00-9 lithium diethyl malonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 3708-36-9 trans-cinnamylmalonic acid 
• 17920-83-1 5-phenyl-4-pentenoic acid 
• 24332-55-6 diethyl 2-cinnamyl-2-methylmalonate 
• 3708-36-9 C₁₂H₁₂O₄ 
• 134039-00-2 N-Methyl-5-phenyl-4-pentenamide 
• 134025-24-4 2-Benzyl-1,4-dimethylpyrrolidine 
• 134025-22-2 N-Methyl-2-methyl-5-phenylpent-4-enylamine 
• 24285-20-9 N-Methyl-5-phenylpent-4-enylamine 
• 4266-03-9 N-Methyl-2-(phenylmethyl)pyrrolidine 

Relevant academic research and scientific papers

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,

MMZNiY-Catalyzed Tsuji–Trost Type of Reaction: A Selective Mono/Bis Allylation of Dicarbonyl Compounds

Abstract: An alternative method to Pd-catalyzed Tsuji–Trost reaction is developed and it provides a simpler route for the selective synthesis of a broad range of mono-/bis-allylated and cinnamylated 1,3-dicarbonyl compounds using MMZNiY catalyst at room temperature. Product selectivity can be controlled by the proper choice of catalyst. The catalyst was also well characterized by SEM, TEM, HRTEM, EDAX and X-ray analysis. Other advantages of catalyst like its ease of preparation, functional tolerance and its reusability are also highlighted.

Catalytic intramolecular carbonyl-ene reaction with ketones: Evidence for a retro-ene process

The ene-process with unsaturated ketones was catalyzed by Lewis acids such as bismuth or indium triflates. Unlike aldehydes, the reverse ene-process occurs with ketones, resulting in incomplete conversions, as shown by control experiments and analysis by ESI-MS.

Palladium-Catalyzed highly diastereoselective oxidative cascade cyclization reactions

Isoquinoline and quinoline have been discovered as novel ligands for palladium-catalyzed oxidative cascade cyclization reactions. With our new catalyst systems (Pd(OAc)2/isoquinoline or quinoline), unsaturated anilides cyclize under an oxygen atmosphere (1 atm) to furnish structurally versatile indoline derivatives in good yields. One C-N bond and two C-C bonds are formed in a single step with excellent diastereoselectivities (dr> 24:1).

Iridium-catalyzed enantioselective allylic alkylation using chiral phosphoramidite ligand bearing an amide moiety

New chiral phosphoramidites with an amide moiety were used for iridium-catalyzed asymmetric allylic alkylation reactions. The best results were obtained with a ligand bearing an oxazolidinone moiety. The reaction of cinnamyl acetate with diethyl sodiomalonate without the use of lithium chloride gave the branched product with 94% ee.

3-Butyl-1-methylimidazolinium borohydride ([bmim][BH4])-a novel reducing agent for the selective reduction of carbon-carbon double bonds in activated conjugated alkenes

A novel ionic reducing reagent, 3-butyl-1-methylimidazolium borohydride ([bmim][BH4]), was synthesized and successfully used for the selective reduction of carbon-carbon double bonds in conjugated alkenes as well as the α,β-carbon-carbon double bonds in highly activated α,β,γ,δ-unsaturated alkenes. The reagent can be regenerated and reused several times without losing its activity.

Trichloroacetylhydrazones: New highly reactive alkylating agents

The behavior of trichloroacylhydrazones as new highly reactive alkylating agents is disclosed; various secondary amines are alkylated within a few minutes at room temperature, and similar alkylating reductions were found with malonates.

Allylic alcohols as substrates for the palladium(0)-catalyzed allylic substitution

A new method has been developed which allows palladium(0)-catalyzed allylic substitution to occur between allylic alcohols and anionic C-nucleophiles: on reaction with Ph3B, the allylic alkoxide 7 is first converted in situ into the more reactive species 8 which then undergoes a Pd(0)-catalyzed reaction with lithiodiethyl malonate via the η3-complex 9.