Category: 31253-08-4

Renaud, Philippe published the artcileRadical carboazidation of alkenes: an efficient tool for the preparation of pyrrolidinone derivatives, Synthetic Route of 31253-08-4, the publication is Angewandte Chemie, International Edition (2002), 41(18), 3460-3462, database is CAplus and MEDLINE.

A one-pot intermol. radical carboazidation of alkenes is reported. The utility of the reaction is demonstrated by the development of a three-component preparation of pyrrolidinones, pyrrolizidinones, and indolizidinones starting from benzenesulfonyl azide, terminal alkenes, and 2-iodo esters.

Angewandte Chemie, International Edition published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Synthetic Route of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Kischkewitz, Marvin published the artcileRadical-polar crossover reactions of vinylboron ate complexes, HPLC of Formula: 31253-08-4, the publication is Science (Washington, DC, United States) (2017), 355(6328), 936-938, database is CAplus and MEDLINE.

Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chem. of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: a 1,2-alkyl/aryl shift from boron to the α-carbon sp² center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chem., enlarging the chem. space of the method. The cascade uses com. starting materials and provides access to perfluoroalkylated alcs., γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.

Science (Washington, DC, United States) published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, HPLC of Formula: 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

de Souza, Carlos A. published the artcileScope and mechanism of the electrochemical Reformatskii reaction of α-haloesters on a graphite powder cathode in aqueous anolyte, Quality Control of 31253-08-4, the publication is Electrochimica Acta (2014), 118-126, database is CAplus.

Six α-haloesters and eighteen carbonyl compounds were submitted to electrochem. coupling on a graphite powder cathode using aqueous anolyte free of organic solvents. Preparative yields of coupling products could be obtained with Et 2-bromoisobutyrate and aromatic aldehydes. Et 2-bromopropionate was much less efficient. Extensive variation of applied potential, electrolyte composition, stoichiometry, catalyst, leaving halogen and activating substituents on the carbonyl compound indicated that the reaction mechanism in most cases proceeds via a radical intermediate generated from the halide reduction Et chloroacetate produced only trace amounts of coupling product, most probably by a carbanionic mechanism.

Electrochimica Acta published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Quality Control of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Baciocchi, Enrico published the artcileSynthesis of γ-haloesters and γ-ketoesters by homolytic addition of carbon radicals generated by α-haloesters and triethylborane to alkenes and silyl enol ethers, HPLC of Formula: 31253-08-4, the publication is Tetrahedron Letters (1994), 35(17), 2763-6, database is CAplus.

γ-Haloesters are efficiently prepared under very mild conditions by addition of electrophilic carbon radicals ·CH(R)CO₂Et (R=H, Me, CO₂Et) generated by XCH(R)CO₂Et (X=Br, iodo)/BEt₃/air in DMSO to alkenes and cycloalkenes. Thus, stirring ICH₂CO₂Et with 1-decene in DMSO in air gave 90% Me(CH₂)₇CHICH₂CH₂CO₂Et. γ-Ketoesters are obtained when silyl enol ethers are used as the substrates.

Tetrahedron Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, HPLC of Formula: 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Baciocchi, Enrico published the artcileHomolytic aromatic substitutions of pentatomic heteroaromatics with electrophilic carbon radicals generated by alkyl halides and triethylborane, Name: Ethyl 2-Iodopropionate, the publication is Tetrahedron Letters (1993), 34(31), 5015-18, database is CAplus.

An efficient homolytic aromatic substitution of pyrroles, furan, and thiophene by ^{â€?/sup>CH₂CO₂Et and â€?/sup>CH(CH₃)CO₂Et has been carried out, the radicals being generated by autoxidation of BEt₃ in the presence of XCH₂CO₂Et and XCH(CH₃)CO₂Et (X = Br, I). Thus, homolytic aromatic substitution reaction of pyrrole with BrCH₂CO₂Et in the presence of BEt₃ in C₆H₆ or DMSO and hexane gave 47% substituted pyrrole I.}

Tetrahedron Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Name: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Baciocchi, Enrico published the artcileHomolytic substitution reactions of electron-rich pentatomic heteroaromatics by electrophilic carbon-centered radicals. Synthesis of α-heteroarylacetic acids, Application of Ethyl 2-Iodopropionate, the publication is Journal of Organic Chemistry (1992), 57(25), 6817-20, database is CAplus.

Efficient and selective homolytic substitutions (55-90% yields) of pyrrole, indole, and some pyrrole derivatives have been carried out using ambiphilic and electrophilic carbon centered radicals, generated in DMSO by Fe²⁺/H₂O₂ and α-cyano-, α-carbonyl-, and α,α’-dicarbonylalkyl iodides. The reaction is highly successful with pyrroles substituted by electron-withdrawing groups, which allowed an efficient synthesis of Tolmetin. A few extensions of this reaction to furan and thiophene are described. Thus, homolytic substitution of pyrrole with ICHRR¹ (R = H, R¹ = CO₂Me, cyano; R = R¹ = CO₂Me) gave 2-substituted pyrroles I.

Journal of Organic Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Application of Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Cheng, Ying published the artcileTransition metal-free 1,2-carboboration of unactivated alkenes, COA of Formula: C5H9IO2, the publication is Journal of the American Chemical Society (2018), 140(20), 6221-6225, database is CAplus and MEDLINE.

A method for transition metal-free 1,2-carboboration of unactivated alkenes with bis(catecholato)diboron as the boron source in combination with alkyl halides as the alkyl component is introduced. The three-component reaction of aryl alkenes ArX(CH₂)_nCH:CH₂ (n = 1-3; X = bond, O) with B₂cat₂ and perfluoroalkyl iodides R^FI as the photoactivated radical source proceeds via a radical pathway on a broad range of unactivated alkenes, and the 1,2-carboboration/transesterification products ArX(CH₂)_nCH(Bpin)CH₂R^F serve as valuable synthetic building blocks. D. functional theory calculations provide insights into the mechanism.

Journal of the American Chemical Society published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, COA of Formula: C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Iwasaki, Masayuki published the artcileRegioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives, Recommanded Product: Ethyl 2-Iodopropionate, the publication is Organic Letters (2018), 20(13), 3848-3852, database is CAplus and MEDLINE.

An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives The reaction proceeds smoothly without any addnl. ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

Organic Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Recommanded Product: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metzger, Jurgen O. published the artcileRadical additions of alkyl 2-haloalkanoates and 2-haloalkanenitriles to alkenes initiated by electron transfer from copper in solvent-free systems, COA of Formula: C5H9IO2, the publication is Liebigs Annalen/Recueil (1997), 2303-2313, database is CAplus.

Alkyl 2-iodoalkanoates and 2-iodoalkanenitriles were added with Cu powder to the 1-alkenes RCH₂CH:CH₂ [R = (CH₂)₇CO₂Me, (CH₂)₄Me, OH, C(CO₂Et)₂CH₂CH:CH₂] and to the alkenes (Z)-R(CH₂)₂CH:CH(CH₂)₂R¹ [R = (CH₂)₅Me, R¹ = (CH₂)₅CO₂Me; R = (CH₂)₅Me, R¹ = (CH₂)₉CO₂Me; R = (CH₂)₈Me, R¹ = (CH₂)₂CO₂Me; RR¹ = bond] to give γ-lactones and 4-iodoalkanenitriles, resp., in very good yields. No solvent was used. The reaction is a free-radical addition initiated by electron transfer from Cu to the activated iodoalkane. Yields were lower using the resp. bromo compounds In-situ formation of the iodo compounds by addition of stoichiometric amounts of NaI to the reaction mixture gave improved yields. In the case of bromomalonates, the addition of NaI proved to be unnecessary. The diastereoselectivity of the addition reaction by relative 1,3-asym. induction was rationalized by consideration of the steric interactions of the substituents in the transition state which is formed in the process of I transfer to the chiral adduct radical.

Liebigs Annalen/Recueil published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, COA of Formula: C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metzger, Juergen O. published the artcileRadical additions of activated haloalkanes to alkenes initiated by electron transfer from copper in solvent-free systems, Product Details of C5H9IO2, the publication is Angewandte Chemie, International Edition in English (1995), 34(8), 902-4, database is CAplus.

The solventless first radical addition of alkyl α-iodocarboxylates or α-iodoalkanenitriles to alkenes over copper metal involves an electron transfer initiated mechanism. The synthetic utility of this method is discussed.

Angewandte Chemie, International Edition in English published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Product Details of C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com