30953-25-4

Upstream product

• 124-38-9 carbon dioxide 
• 2687-12-9 cinnamyl chloride 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 2327-99-3 1-phenylpropadiene 
• 147609-46-9 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 42817-44-7 (E)-N,N-dimethyl-3-phenylprop-2-en-1-amine 
• 1421354-42-8 (2E)-N,N,N-trimethyl-3-phenylprop-2-en-1-aminium trifluoromethanesulfonate 
• 300-57-2 allylbenzene 
• 85217-69-2 cinnamyl methyl carbonate 
• 21040-45-9 Cinnamyl acetate 
• 873-66-5 1-propenylbenzene 

Downstream Products

• 3127-67-1 2-phenyl-but-2-enoic acid 
• 25522-59-2 benzeneacetic acid,α-ethenyl, methyl ester 
• 108179-73-3 (+)-4-methoxybiphenyl 2-phenyl-3-butenoate 
• 108179-74-4 (-)-(4-methoxyphenoxy)carbonylphenyl 2-phenyl-3-butenoate 
• 108179-75-5 (+)-4-(4-methoxyphenoxy)phenylcarbonylphenyl 2-phenyl-3-butenoate 
• 1037175-93-1 C₁₈H₂₆N₂O₂ 
• 4393-21-9 1-(phenyl)allylamine 
• 74394-96-0 3-phenyl-2-propenyl thiocyanate 
• 20332-96-1 1,2-dicinnamyldisulfane 
• 96631-56-0 (S)-3-Methyl-2-phenyl-hexahydro-pyrrolo[1,2-b]isoxazole-2-carboxylic acid methyl ester 
• 96631-55-9 3-methoxycarbonyl-2-methyl-3-phenyl-2,3,3a,4,5,6-hexahydropyrrolo<1,2-b>isoxazole 
• 96631-58-2 methyl 2,3,3aα,4,5,6-hexahydropyrrolo<1,2-b>isoxazol-2α-yl phenylacetate 
• 96631-57-1 1-aza-4β-hydroxy-3α-phenyl-5aαH-bicyclo<4.3.0>nonan-2-one 
• 50415-84-4 (Z)-2-phenyl-but-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Nickel-catalyzed electrocarboxylation of allylic halides with CO2

Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, temperature and additive. β,γ-Unsaturated carboxylic acids were obtained in moderate to good yields and with high chain selectivity. This reaction shows tolerance to functional groups. In addition, cyclic voltammetry was performed to provide the possible mechanism of nickel-catalyzed CO2allylation.

Electroreductive Cobalt-Catalyzed Carboxylation: Cross-Electrophile Electrocoupling with Atmospheric CO2

The chemical use of CO2 as an inexpensive, nontoxic C1 synthon is of utmost topical interest in the context of carbon capture and utilization (CCU). We present the merger of cobalt catalysis and electrochemical synthesis for mild catalytic carb

Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: Scope and mechanistic insights

A caesium fluoride-mediated hydrocarboxylation of olefins is disclosed that does not rely on precious transition metal catalysts and ligands. The reaction occurs at atmospheric pressures of CO2 in the presence of 9-BBN as a stoichiometric reductant. Stilbenes, β-substituted styrenes and allenes could be carboxylated in good yields. The developed methodology can be used for preparation of commercial drugs as well as for gram scale hydrocarboxylation. Computational studies indicate that the reaction occurs via formation of an organocaesium intermediate.

Silver encapsulated copper salen complex: Efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2

An active catalyst, [Cu]?Ag composite, was synthesized for the first time and used as a cathode for electrocarboxylation of cinnamyl chloride with CO2. β,γ-Unsaturated carboxylic acids were obtained with excellent yield and moderate selectivity. Moreover, reasonable yields and selectivities of carboxylic acids were also achieved with several allylic halides and aryl halides.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.

Synthesis of 2-aryloxy butenoates by copper-catalysed allylic C-H carboxylation of allyl aryl ethers with carbon dioxide

Efficient synthesis of 2-aryloxy-3-butenoic acid esters by allylic C-H bond carboxylation of allyl aryl ethers with CO2 has been achieved through deprotonative alumination with an aluminium ate compound (iBu3Al(TMP)Li) followed by NHC-copper-catalysed carboxylation of the resulting aryloxy allylaluminum species. Functional groups such as halogens (F, Cl, Br, I), CF3, amino, methylthio, silyloxy and hetero aromatic groups survived the reaction conditions. The regio- and stereoselective transformation (isomerization) of 2-aryloxy-3-butenoate products to (Z)-2-aryloxy-2-butenate isomers has also been achieved in the presence of a catalytic amount of DBU. These transformations thus constitute an efficient protocol for the divergent synthesis of both 2-aryloxy-3- and 2-butenonates from a single allyl aryl ether substrate using CO2 as a C1 building block.

Regioselective copper-catalyzed carboxylation of allylboronates with carbon dioxide

In the presence of a Cu(I)/NHC catalyst, the reactions of allylboronic pinacol esters with CO2 (1 atm) are highly regioselective, giving exclusively the more substituted β,γ-unsaturated carboxylic acids in most cases. A diverse array of substituted carboxylic acids can be prepared via this method, including compounds featuring all-carbon quaternary centers.

Electrochemical carboxylation of benzylic carbonates: Alternative method for efficient synthesis of arylacetic acids

Electrochemical carboxylation of benzylic carbonates was successfully performed as an alternative method for the synthesis of phenylacetic acids by using a one-compartment cell equipped with a Pt plate cathode and an Mg rod anode in CH3CN to afford the corresponding phenylacetic acids in good yields.

Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex

Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful β,γ-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of σ-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO2 in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol. Copyright

New chiral polysiloxanes prepared from derivatives of (+)- or (-)-2-phenyl-3-butehoic acid, (r)-l-hepten-3-ol and (r)-l-cyclohexyl-2-propen-1-ol

A series of new polysiloxanes containing chiral side groups has been prepared. These polymers were prepared by hydrosilylating chiral alkene derivatives onto polyhydromethylsiloxane. The alkene derivatives were prepared from (+) or (-)-2-phenyl-3-butenoic acid, (R)-1-hepten-3-ol and (R)-1-cyclohexyl-2-propen-1-ol. Polysiloxanes containing racemic substituents were also prepared fron derivatives of racemic 3-buten-2-ol. The polysiloxanes containing biphenyl carboxylate derivatives (11a-13a) had liquid crystalline properties. These polymers were prepared for use as stationary phases for capillary gas and supercritical fluid chromatography.