81981-18-2

Upstream product

• 81981-17-1 3-acetoxy-3-cyano-1-(4-chlorophenyl)propene 
• 1615-02-7 p-chlorocinnamic acid 
• 624-75-9 iodoacetonitrile 
• 1679-18-1 4-Chlorophenylboronic acid 
• 109-75-1 but-3-enenitrile 
• 81981-17-1 Acetic acid (E)-3-(4-chloro-phenyl)-1-cyano-allyl ester 
• 1073-67-2 4-vinylbenzyl chloride 
• 590-17-0 cyanomethyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 557-21-1 zinc(II) cyanide 
• 53915-69-8 allenyltributylstannane 
• 1075-77-0 4-chlorocinnamaldehyde 

Relevant academic research and scientific papers

Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles

An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.

Cu-Catalyzed atom transfer radical addition reactions of alkenes with α-bromoacetonitrile

A practical, simple, and efficient copper-catalyzed atom transfer radical addition reaction of alkenes with α-bromoacetonitrile is realized. With this methodology, various γ-bromonitriles and β,γ-unsaturated nitriles were efficiently constructed.

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

Method for synthesizing diaryl pyrrole compound

The invention relates to a method for synthesizing a diaryl pyrrole compound. The method comprises a reaction route shown in the specification. The method comprises the following steps: S1, in the presence of a palladium catalyst, organic ligand, an oxidant and an acid compound, enabling a compound of formula (I) and a compound of formula (2) to react in an organic solvent, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (3); S2, in the organic solvent, enabling the compound of formula (3) to be subjected to a self-cyclization reaction in thepresence of the oxidant, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (4); S3, in the presence of nitrogen, enabling the compound of formula (4)and a compound of formula (5) to react in the solvent in the presence of the palladium catalyst, the organic ligand, the oxidant and the acid compound, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (6). By adopting the method, different steps are creatively optimized with multiple technical characteristics, completely new synthesis methods andsynthesis routes are provided for preparation of the compound, and good industrial prospects and potential application values can be achieved.

Method for synthesizing pyrrole derivative

The invention relates to a method for synthesizing a pyrrole derivative represented by a formula (6) shown in the description. The synthesis method has a reaction route shown in the description. The synthesis method comprises the following steps: S1: subjecting a compound represented by a formula (3) shown in the description to a self-cyclization reaction in the presence of an oxidant in an organic solvent, and carrying out aftertreatment after the reaction ends, so as to obtain a compound represented by a formula (4) shown in the description; and S2: subjecting the compound represented by theformula (4) and a compound represented by a formula (5) shown in the description to a reaction in the presence of a palladium catalyst, an organic ligand and an acidic compound in a solvent in a nitrogen atmosphere, and carrying out aftertreatment after the reaction ends, so as to obtain a compound represented by a formula (6) shown in the description. According to the method, through creativelyoptimizing a plurality of technical features of each step, a bran-new synthesis method and synthesis route are provided for preparing this kind of compounds, and thus, the method has a good industrialization prospect and a potential application value.

Organotin Nucleophiles. 5. Palladium-Catalyzed Allylic Propargylation with Allenylstannane

Allenyltrialkylstannanes were found to react with various allylic acetates in the presence of catalytic amounts of Pd(PPh3)4 under mild neutral conditions, providing a novel approach for obtaining the 1,5-enyne carbon skeleton.The regioselectivity of propargylation depends largely on the electron-withdrawing properties of the substituents at the two ends of the allylic system: substitution occurs at the end of closer proximity to the more electronegative group.Allylic cyanohydrin acetates are substituted at a position α to the cyano group along with formation of a reduced side product.Several mechanistic aspects of these reactions are discussed.

ORGANO TIN NUCLEOPHILES III. PALLADIUM CATALYZED REDUCTIVE CLEAVAGE OF ALLYLIC HETEROSUBSTITUENTS WITH TIN HYDRIDE

Tributyl tin hydride, serving as an efficient hydride transfer agent, allows highly chemoselective palladium catalyzed reductions of allylic heterosubstituents even in presence of aldehydes, benzyl acetate and benzyl chloride.