5558-47-4

Upstream product

• 1077-16-3 hexylbenzene 
• 100-42-5 styrene 
• 109-72-8 n-butyllithium 
• 124-38-9 carbon dioxide 
• 37629-82-6 (Z)-α-phenyl-β-(2-thienyl)acrylonitrile 
• 628-17-1 amyl iodide 
• 101-41-7 benzeneacetic acid methyl ester 
• 1534433-67-4 methyl 2-phenylheptanoate 
• 111-14-8 oenanthic acid 
• 108-95-2 phenol 

Downstream Products

• 189127-40-0 (R)-2-phenyl-heptanoic acid 
• 14387-53-2 (+/-)-2-phenyl-heptanoic acid amide 
• 1365842-06-3 4-methyl-N-(2-phenylheptyl)benzenesulfonamide 

Relevant academic research and scientific papers

Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

METHOD FOR PRODUCING CARBOXYLIC ACID ESTER

To provide a production method capable of obtaining a carboxylic acid ester from a reaction of a carboxylic acid with a hydroxy compound at a milder reaction temperature.SOLUTION: There is provided a method for producing a carboxylic acid ester capable of obtaining a carboxylic acid ester by reacting a carboxylic acid with a hydroxy compound in the presence of a catalyst containing a compound (A) and a compound (B), wherein the compound (A) is a salt composed of an anion portion and a cation portion, the anion portion is an anion derived from a strong acid, the cation portion is at least one selected from the group consisting of a lithium ion and a magnesium ion and the compound (B) is a compound in which at least one hydroxy group is bonded to a boron atom.SELECTED DRAWING: None

Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand

A unique example of Pd-catalyzed decarboxylative dehydrogenation of fully substituted N-acyl allyl enol carbonates is enabled by a new electron deficient phosphinooxazoline (PHOX) ligand. The reaction proceeds from the Z-enol carbonate to provide dehydrogenation products exclusively in high E/Z selectivity, while the E-enol carbonate provides the α-allylation product with only minor dehydrogenation. The reaction proceeds with a broad scope of Z-enol carbonates derived from N-acyl indoles to furnish acyclic formal α,β-unsaturated ester equivalents.

Organolithium addition to styrene and styrene derivatives: Scope and limitations

Styrene and a range of aryl-substituted styrene derivatives are shown to undergo efficient carbolithiation-trapping reactions in diethyl ether at -78 to -25 °C. The reactivities of different types of organolithium reagents were found to be: tertiary, secondary > primary; ? alkenyl, methyl, phenyl. Electron donating groups (e.g. methoxy and dialkylamino) at the ortho- or para- positions of the benzene ring deactivate the double bond towards organolithium addition, but their reactions with butyllithium can be facilitated by using TMEDA as co-solvent. 2-Benzyloxystyrene and 2-allyloxystyrene undergo efficient carbolithiation at -78 °C, but at room temperature alkyl transfer occurs, generating the corresponding alkylated phenol. 2-Vinylnaphthalene also undergoes carbolithiation-carboxylation in reasonable yield.

Organolithium additions to styrene are synthetically viable

In diethyl ether at -78 to -25°C, styrene undergoes efficient addition reactions with a range of alkyllithium reagents, and the intermediate benzyllithiums can be trapped (e.g. with carbon dioxide and chlorotrimethylsilane); two aryl-substituted styrenes are shown to react in a similar manner.