35256-93-0

Upstream product

• 18496-54-3 phenylbutyric acid chloride 
• 124-40-3 dimethyl amine 
• 100-42-5 styrene 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 1821-12-1 4-Phenylbutyric acid 
• 16520-62-0 4-Phenyl-1-butyne 
• 506-59-2 N,N-dimethylammonium chloride 
• 300-57-2 allylbenzene 
• 201230-82-2 carbon monoxide 
• 506-68-3 bromocyane 

Downstream Products

• 100420-14-2 methyl 8-phenyl-3,5-dioxooctanoate 
• 1202-55-7 4-phenyl-1-(N,N-dimethylamino)butane 
• 1449300-08-6 4-phenyl-N-(quinolin-8-yl)butanamide 
• 3056-71-1 N-phenyl-4-phenylbutyramide 

Relevant academic research and scientific papers

Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins

Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.

Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.

Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides

A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C-X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.

C-Alkylation of N-alkylamides with styrenes in air and scale-up using a microwave flow reactor

C-Alkylation of N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to 65 g h-1 product) was demonstrated using a Microwave Flow reactor, as the first example of a C-alkylation reaction using styrenes in continuous flow.

Palladium-Catalyzed Hydrocarbonylative C-N Coupling of Alkenes with Amides

An efficient palladium-catalyzed hydrocarbonylative C-N coupling of alkenes with amides has been developed. The reaction was performed via hydrocarbonylation of alkenes, followed by acyl metathesis with amides. Both intermolecular and intramolecular react

Rhodium-catalyzed oxygenative addition to terminal alkynes for the synthesis of esters, amides, and carboxylic acids

A gem of a couple: The title reaction of terminal alkynes with O and Nnucleophiles proceeds in the presence of [Rh(cod)Cl}2], P(4-FC 6H4)3, and 4-picoline N-oxide. Alcohols, amines, and water add to the terminal alkynes to give esters, amides, and carboxylic acids, respectively. The reaction involves formation of a rhodium vinylidene, oxidation to a ketene by oxygen transfer, and nucleophilic addition.

The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides

The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.

Synthesis of quaternary alkylammonium sulfobetaines

A series of quaternary alkylammonium sulfobetaines of general formula RN+(CH3)2(CH2)nSO 3-, where n = 2-4, have been synthesised by reacting the corresponding N,N-dimethylamines with either sodium 2-chloroethanesulfonate (n = 2), 1,3-propane-sultone (n = 3), or 1,4-butanesultone (n = 4). Full details of the preparation of the required N,N-dimethylamines are reported.

ALKYLATION OF N-SUBSTITUTED AMIDES OF CARBOXYLIC ACIDS BY STYRENE IN THE PRESENCE OF POTASSIUM HYDROXIDE

The reaction of N,N-dimethylacetamide with styrene in the dimethyl sulfoxide-potassium hydroxide system leads to the formation of α-C-alkylated reaction products.It was established that substitution of the dimethyl sulfoxide by the initial amide makes it possible to increase the total yield of the monoalkylation and dialkylation products to 87 percent.From N-ethylacetamide and styrene under analogous conditions the N-alkylation product was obtained (37 percent).