Tag: M.W=150-200

Wang, Xin-Gang published the artcileThree-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes, Synthetic Route of 401-55-8, the publication is Journal of the American Chemical Society (2019), 141(35), 13914-13922, database is CAplus and MEDLINE.

Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent reactions can enable the efficient and step-economical construction of complex mol. scaffolds from simple precursors. Here, an unprecedented three-component direct C-H addition was achieved in the challenging meta-selective fashion. Fluoroalkyl halides and a wide range of alkenes, including vinylarenes, unactivated alkenes, and internal alkenes, were employed as the coupling partners of arenes in this strategy. The detailed mechanism presented is supported by kinetic isotope studies, radical clock experiments, and d. functional theory calculations Moreover, this strategy provided access to various fluoride-containing bioactive 1,1-diarylalkanes and other challenging synthetically potential products.

Journal of the American Chemical Society published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C7H6Cl2, Synthetic Route of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Xin-Gang published the artcileRuthenium(II)-catalyzed selective C-H difluoroalkylation of aniline derivatives with pyrimidyl auxiliaries, Application In Synthesis of 401-55-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(68), 9541-9544, database is CAplus and MEDLINE.

A ruthenium-catalyzed alternative para- and meta-difluoroalkylation of anilines is herein reported. The reaction tolerates a broad range of aniline derivatives and provides a convenient approach for accessing the corresponding para/meta-selective difluoroalkylated products. Mechanism studies demonstrated that the initial C_Ar-H and N-H cycloruthenation is the pivotal step in achieving remote C-H difluoroacetylation.

Chemical Communications (Cambridge, United Kingdom) published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C12H10O4S, Application In Synthesis of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Zhao, Binlin published the artcileAn Olefinic 1,2-Boryl-Migration Enabled by Radical Addition: Construction of gem-Bis(boryl)alkanes, Recommanded Product: Ethylbromofluoroacetate, the publication is Angewandte Chemie, International Edition (2019), 58(28), 9448-9452, database is CAplus and MEDLINE.

A series of in situ formed alkenyl diboronate complexes from alkenyl Grignard reagents (com. available or prepared from alkenyl bromides and Mg) with B₂Pin₂ (bis(pinacolato)diboron) react with diverse alkyl halides by a Ru photocatalyst to give various gem-bis(boryl)alkanes. Alkyl radicals add efficiently to the alkenyl diboronate complexes, and the adduct radical anions undergo radical-polar crossover, specifically, a 1,2-boryl-anion shift from boron to the α-carbon sp² center. This transformation shows good functional-group compatibility and can serve as a powerful synthetic tool for late-stage functionalization in complex compounds Measurements of the quantum yield reveal that a radical-chain mechanism is operative in which the alkenyl diboronates acts as reductive quencher for the excited state of the photocatalyst.

Angewandte Chemie, International Edition published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C11H22N2O4, Recommanded Product: Ethylbromofluoroacetate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Songyi published the artcileTransition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes, Formula: C8H17Br, the publication is Journal of Organic Chemistry (2022), 87(6), 4291-4297, database is CAplus and MEDLINE.

A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane was developed. This protocol is operationally convenient and features a rapid reaction and good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl tri-Me stannanes were prepared in moderate to excellent yields. The success of the gram-scale procedure and tandem Stille coupling reaction has allowed this protocol to demonstrate potential for application in organic synthesis. Both exptl. and theor. studies reveal the mechanistic details of this stannylation reaction.

Journal of Organic Chemistry published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Formula: C8H17Br.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Beniazza, Redouane published the artcileFree-Radical Carbo-Alkenylation of Olefins: Scope, Limitations and Mechanistic Insights, Quality Control of 401-55-8, the publication is Chemistry – A European Journal (2017), 23(10), 2439-2447, database is CAplus and MEDLINE.

The three-component free-radical carbo-alkenylation of electron-rich olefins has been studied, varying the substitution pattern in the alkene, in the radical precursor and in the final acceptor. New vinylsulfones were also prepared and their reactivity investigated. The scope and limitations of the process was established, and the reaction mechanism clarified using selected dienes as radical clocks. It was thus recognized that the reversible addition onto the olefin of the released sulfonyl group is an important event, which should not be overlooked when using such multicomponent carbo-alkenylation reactions.

Chemistry – A European Journal published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Quality Control of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Cui, Ning published the artcileNickel-Catalyzed Reductive Coupling of γ-Metalated Ketones with Unactivated Alkyl Bromides, Application In Synthesis of 111-83-1, the publication is Organic Letters (2022), 24(22), 3987-3992, database is CAplus and MEDLINE.

A nickel-catalyzed reductive cross-coupling reaction of aryl cyclopropyl ketones with easily accessible unactivated alkyl bromides to access aryl alkyl ketones was developed. This strategy facilitated access to various of γ-alkyl substituted ketones via ring opening of cyclopropyl ketones (26 examples, 50-90% yield). Initial mechanistic studies revealed that the reaction proceeds via a radical cleavage of the alkyl bromide.

Organic Letters published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Application In Synthesis of 111-83-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Zhong-Yuan published the artcileRuthenium-Catalyzed meta-Selective C-H Mono- and Difluoromethylation of Arenes through ortho-Metalation Strategy, Application of Ethylbromofluoroacetate, the publication is Chemistry – A European Journal (2017), 23(14), 3285-3290, database is CAplus and MEDLINE.

The first example for the ruthenium-catalyzed ligand-directed meta-selective C-H mono- and difluoromethylation is developed, affording a variety of new meta-mono- and difluoromethylated 2-phenylpyridines, 2-phenylpyrimidines, and 1-phenylpyrazoles in moderate-to-good yields. This new transformation exhibits broad substrate scope, good functional group tolerance, and high efficiency, and offers a practical approach to synthesize mono- and difluoromethylated arenes. Mechanistic studies indicate that a reaction pathway involving palladium-initiated radical species is involved in the catalytic cycle. The new dual catalytic system consisting of compatible ruthenium(II) and palladium(0) complexes enables the key processes of C-H activation and mono-/difluoromethyl-radical formation to occur and achieves the meta-selective functionalization efficiently. In addition, the present protocol can also be extended to non-fluoromethylation.

Chemistry – A European Journal published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Application of Ethylbromofluoroacetate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Pan, Xiujiao published the artcileBiosafety-inspired structural optimization of triazolium ionic liquids based on structure-toxicity relationships, Related Products of bromides-buliding-blocks, the publication is Journal of Hazardous Materials (2022), 424(Part_C), 127521, database is CAplus and MEDLINE.

Ionic liquids (ILs), owing to their low vapor pressure and excellent solvating ability, are being increasingly applied in various industries to replace highly toxic organic solvents. They mainly pollute aquatic environment and soils, directly endangering eco-environment and human health. Therefore, it is critical to understand and optimize structural motifs of ILs with reduced toxicity. Considering human oral exposure is the major route, our investigations employed a human cell panel (modeling oral exposures) including human stomach (GES-1), intestinal (FHC), liver (HepG2) and kidney (HEK293) cells using a series of exptl. and computational approaches to explore the cytotoxicity and mol. mechanism of ILs. We discovered that the cytotoxicity of triazolium and imidazolium ILs was human cell line-dependent with cytotoxicity in an order of FHC > GES-1 > HepG2 > HEK293. For this reason, a toxicity assay using a single cell line was highly inappropriate. Compared to anions (Br-, OTs-, OTMBS-) we tested, the cation of ILs played a major role in causing cytotoxicity. Ionic liquids with cations having longer hydrophobic sidechains (IL09 vs. IL01) readily insert into cell membranes with enhanced membrane and lipidomic perturbations, induce cytotoxicity by triggering cell cycle arrest and apoptosis. Reducing sidechain length and incorporating three nitrogen atoms (triazolium) instead of two (imidazolium) in the cation core alleviated cytotoxicity by reducing cell membrane perturbations and cell function interference. These findings provide important guiding principles for the design of the next-generation of “green” and safe ILs.

Journal of Hazardous Materials published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Zhang, Pengbo published the artcileCopper and Photocatalytic Radical Relay Enabling Fluoroalkylphosphorothiolation of Alkenes: Modular Synthesis of Fluorine-Containing S-Alkyl Phosphorothioates and Phosphorodithioates, COA of Formula: C4H6BrFO2, the publication is Organic Letters (2021), 23(23), 9267-9272, database is CAplus and MEDLINE.

A photoredox and copper-catalyzed fluoroalkylphosphorothiolation of activated and unactivated alkenes via a radical relay mechanism is reported. By employing fluoroalkyl halides as radical precursors and P(O)SH or P(S)SH compounds as coupling partners, a wide range of β-monofluoroalkyl-, -difluoroalkyl-, -trifluoromethyl-, or -perfluoroalkyl-substituted S-alkyl phosphorothioates and phosphorodithioates can be easily constructed under mild conditions with good functional group tolerance. Furthermore, this modular reaction system can be successfully applied to late-stage functionalization of bioactive mols.

Organic Letters published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C8H5F3O2S, COA of Formula: C4H6BrFO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Zhang, Zhong published the artcileVisible-Light-Promoted Oxy-Difluoroalkylation Of Aryl Alkynes For The Synthesis Of β-Fluoroenones And α-Difluoroalkyl Ketones, Synthetic Route of 401-55-8, the publication is Advanced Synthesis & Catalysis (2021), 363(13), 3348-3353, database is CAplus.

A method for regio-, stereoselective synthesis of (E)-β-fluoroenones I [R = H, Et, nPr; R¹ = CO₂Et, C(O)NEt₂, P(O)(OEt)₂, pyrrolidin-1-yl; Ar = Ph, 4-MeC₆H₄, 4-BrC₆H₄, etc.] was synthesized via visible light irradiated oxy-difluoroalkylation of alkynes using di-fluoroacetates and water as oxygen source, potassium carbonate as base. Also, α-difluoroalkyl ketones II [Ar¹ = Ph, 2-thienyl, 4-ClC₆H₄, etc.; R² = Me, Et, nPr, etc.] were obtained using phenylpyridine as base under same reaction conditions. These transformations featured mild condition, wide functional tolerance and step economy. The large-scale transformations and further derivatization showed its potential application in organic synthesis.

Advanced Synthesis & Catalysis published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is 0, Synthetic Route of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary