42858-44-6

Upstream product

• 16141-22-3 ethyl 3-hydroxy-2-phenylbutanoate 
• 86387-67-9 ethyl 2,3-dioxo-5-methyltetrahydrofuran-4-carboxylate 
• 3076-54-8 phenyllead(IV) triacetate 
• 4341-76-8 Ethyl 2-butynoate 
• 98-80-6 phenylboronic acid 
• 20469-72-1 phenylboronic acid-d₂ 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Relevant academic research and scientific papers

Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides

An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.

Visible-Light-Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition

The [2+2] photocycloaddition is the most valuable and intensively investigated photochemical process. Here we demonstrate that irradiation of N-acryloyl heterocycles with blue LED light (440 nm) in the presence of an IrIII complex leads to efficient and high yielding fused γ-lactam formation across a range of substituted heterocycles. Quantum calculations show that the reaction proceeds via cyclization in the triplet excited state to yield a 1,4-diradical; intersystem crossing leads preferentially to the closed shell singlet zwitterion. This is geometrically restricted from undergoing recombination to yield a cyclobutane by the planarity of the amide substituent. A prototropic shift leads to the observed bicyclic products in what can be viewed as an interrupted [2+2] cycloaddition.

Single-isomer trisubstituted olefins from a novel reaction of (E)-βchloro-α-iodo-α,β-unsaturated esters and amides

(Chemical Equation Presented) (E)-β-Chloro-α-iodo-α, β-unsaturated esters are converted to single isomer trisubstituted olefins bearing three different carbon substituents by cross-coupling under reflux. Mechanistic investigations suggest that this process transfers a hydrogen from the boronic acid to the α-position of the substrate and then introduces an aryl group to the β-position of the intermediate template while replacing chloride. The reaction is highly stereoselective, showing preference for the E-isomer. The process proceeds through (E)-β-chloro-α-aryl-α, β-unsaturated esters that are transformed efficiently into the corresponding E-products through stereoselective Suzuki-type reactions giving single isomers. The observed stereo-chemistry is apparently enabled by the intermediacy of a palladium allenoate. The reaction involves a catalytic cycle in which PdII is reduced to Pd0 through the formation of biaryl-coupled products.

Pd-catalyzed addition of organoboronic acids to alkynes at room temperature

Combination of Pd(OAc)2 with 2-bromo-1,3-bis- [diphenylphosphenomethyl)]benzene (1) or 2-bromo-1,3-bis-[di-tert- butylphosphenomethyl)]benzene (3) catalyzed hydroarylations and hydroalkenylations of various alkynes more efficiently in terms of

The Chemistry of Aryllead Tricarboxylates. Synthesis of Some α-Aryl α,β-Unsaturated Carbonyl Compounds

The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield.This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates.It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of α-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.