Category: 576-83-0

Shon, Jong-Hwa; Sittel, Steven; Teets, Thomas S. published the artcile< Synthesis and characterization of strong cyclometalated iridium photoreductants for application in photocatalytic aryl bromide hydrodebromination>, Computed Properties of 576-83-0, the main research area is iridium photoredox catalyst hydrodebromination.

A series of potent bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands is described. Structure-property anal. reveals that substituent modification of the NacNac ligands has a large effect on the ground-state IrIV/IrIII potential, which shifts cathodically as the NacNac is made more electron-rich. In addition, the excited-state IrIV/*IrIII potentials are ca. 300-500 mV more neg. than that of fac-Ir(ppy)3 (ppy = 2-phenylpyridine), indicating that these compounds have much more reducing excited states. Rate constants for excited-state electron transfer between these photosensitizers and benzophenone are ∼2-3 times faster than fac-Ir(ppy)3, demonstrating that these complexes are both kinetically and thermodynamically more potent for excited-state electron transfer. We use these photosensitizers to optimize a simple reaction procedure for photocatalytic debromination of aryl bromide substrates, which requires only the photosensitizer, blue light, and an amine base, without silanes or other additives that are used in previously reported methods.

ACS Catalysis published new progress about Aromatic nitrogen heterocycles, aromatic nitrogen heterocycle transition metal complexes Role: CAT (Catalyst Use), PRP (Properties), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Computed Properties of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Zhao-Zhao; Zhao, Jia-Hui; Gou, Xue-Ya; Chen, Xi-Meng; Liang, Yong-Min published the artcile< Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex>, Product Details of C9H11Br, the main research area is aryl alkyl halide amine free radical reductive dehalogenation; dehalogenative deuteration reductive cyclization addition cycloaddition arylation.

Herein, a novel photo-induced amine-free radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described,. Which reveals excellent functional group compatibility and broad substrate scope. Extensional transformations for reductive cyclization, dehalogenative deuteration, and intra- and intermol. radical addition can be achieved smoothly. Mechanistic studies indicate a single-electron photoredox catalytic system with inactivated solvent as the hydrogen atom donor.

Organic Chemistry Frontiers published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Product Details of C9H11Br.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sinai, Adam; Simko, Daniel Cs.; Szabo, Fruzsina; Paczal, Attila; Gati, Tamas; Benyei, Attila; Novak, Zoltan; Kotschy, Andras published the artcile< Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application>, Safety of 2,4,6-Trimethylbromobenzene, the main research area is aryl diadamantyl phosphine ligand palladium catalyst preparation coupling; Buchwald Hartwig tosyl hydrazone coupling.

Synthesis, temperature-dependent NMR structure study and use of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In the authors’ study, the authors demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

European Journal of Organic Chemistry published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Safety of 2,4,6-Trimethylbromobenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Shaofei; Vayer, Marie; Noel, Florent; Vukovic, Vuk D.; Golushko, Andrei; Rezajooei, Nazanin; Rowley, Christopher N.; Leboeuf, David; Moran, Joseph published the artcile< Unlocking the Friedel-Crafts arylation of primary aliphatic alcohols and epoxides driven by hexafluoroisopropanol>, Reference of 576-83-0, the main research area is alc preparation regioselective; epoxide arene ring opening Friedel Crafts arylation Bronstedacid catalyst; arylethane preparation; aliphatic alc arene Friedel Crafts arylation Bronsted acid catalyst.

The limitations thar easily overcome using Bronsted acid catalysis in hexafluoroisopropanol (HFIP) as a solvent were reported. Electron-poor aromatic epoxides and aliphatic epoxides undergo stereospecific arylation to give alcs. RC(R1)(Ar)CH2OH/RCH(OH)CH(Ar)OH, and based on the reaction conditions, it can partake in a second nucleophilic substitution with a different arene ArH in one pot. Ph ethanols R3(CH2)2OH (R3 = Ph, 2,6-dichlorophenyl, 2,4,6-trimethylphenyl, etc.) react through a phenonium intermediate, whereas simple aliphatic alcs. e.g., cyclopentanol participate in a rare intermol. SN2 Friedel-Crafts process, delivering linear products e.g., 1,3,5-trimethyl-2-phenethylbenzene exclusively. In this work, an alternative to metal-catalyzed cross-couplings was provided for accessing important scaffolds, and widening the range of applications of the Friedel-Crafts reaction.

Chem published new progress about Aralkyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Reference of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tien, Chieh-Hung; Trofimova, Alina; Holownia, Aleksandra; Kwak, Branden S.; Larson, Reed T.; Yudin, Andrei K. published the artcile< Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations>, Computed Properties of 576-83-0, the main research area is CO surrogate palladium catalyzed carbonylative transformation; aminocarbonylation alkoxycarbonylation Sonogashira Zuzuki Miyaura coupling catalyst; C1 building blocks; CO surrogates; carbonylation; carboxyboronates; palladium catalysis.

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcs., and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki-Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.

Angewandte Chemie, International Edition published new progress about Alkoxycarbonylation. 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Computed Properties of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Gensch, Tobias; Smith, Sleight R.; Colacot, Thomas J.; Timsina, Yam N.; Xu, Guolin; Glasspoole, Ben W.; Sigman, Matthew S. published the artcile< Design and Application of a Screening Set for Monophosphine Ligands in Cross-Coupling>, Application of C9H11Br, the main research area is arene aryl boronic acid palladium phosphine Suzuki coupling; bromobenzene aminobenzimidazole palladium phosphine chemoselective Buchwald Hartwig amination.

A virtual library, kraken, which is representative of the monodentate P(III)-ligand chem. space, was utilized as the basis to represent the discrete ligands as continuous variables. Using dimensionality reduction and clustering techniques, a Phosphine Optimization Screening Set (PHOSS) of 32 com. available ligands was suggested that samples this chem. space completely and evenly. The application of this screening set was presented in the identification of active catalysts for various cross-coupling reactions and show how well-distributed sampling of the chem. space facilitates identification of active catalysts. Furthermore, how proximity in ligand space can be a useful guide to further explore ligands when very few active catalysts are known was demonstrated.

ACS Catalysis published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Application of C9H11Br.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nishii, Yuji; Ikeda, Mitsuhiro; Hayashi, Yoshihiro; Kawauchi, Susumu; Miura, Masahiro published the artcile< Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides>, HPLC of Formula: 576-83-0, the main research area is arene triptycenyl sulfide catalyst electrophilic aromatic halogenation halosuccinimide regioselective; aryl halide preparation.

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray anal. A preliminary computational study disclosed that the π system of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Journal of the American Chemical Society published new progress about Aromatic compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, HPLC of Formula: 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Umakoshi, Yuki; Takemoto, Yusuke; Tsubouchi, Akira; Zhdankin, Viktor V.; Yoshimura, Akira; Saito, Akio published the artcile< Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis>, Quality Control of 576-83-0, the main research area is oxazole preparation; amide arene dehydrogenative cycloisomerization arylation hypervalent iodine catalyst.

Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C-C bond formation between the generated heterocycles and unfunctionalized arenes. Here, authors describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp3)-C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes.

Advanced Synthesis & Catalysis published new progress about Amides Role: RCT (Reactant), RACT (Reactant or Reagent) (N-propargyl carboxamides). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Quality Control of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dong, Zhaowen; Schmidtmann, Marc; Mueller, Thomas published the artcile< Potassium Salts of 2,5-Bis(trimethylsilyl)-Germolide: Switching between Aromatic and Non-Aromatic States>, Application In Synthesis of 576-83-0, the main research area is potassium salt trimethylsilyl germolide preparation crystal mol structure reactivity; switching aromatic non aromatic state mesityl silyl germolole; X-ray diffraction; aromaticity; density functional calculations; germacyclopentadienyl anion; germanium.

The reduction of a 1-mesityl-2,5-bis-trimethylsilylchlorogermole 8 with KC8 is reported. While the reaction with one equivalent of KC8 gave the dimer with a Ge-Ge bond 10, excess of KC8 (four equivalent) resulted in the formation of the potassium salt of the germole dianion, 11 with reductive cleavage of the Ge-C bond. Careful reduction with two equivalent of KC8 in THF provided the potassium salt of the planar germolide 5. Its solid-state structure revealed contact ion pairs with the potassium ion η5-coordinated to the germacyclopentadienide ring. The mol. structure of the anion indicates a high degree of cyclic electron delocalization, in agreement with results from DFT calculations Separation of the ion pair by complexation of the potassium ions with 18-crown-6 triggers the isomerization to germolide 6, which is characterized by a pyramidal coordination sphere of the germanium atom and a localized diene structure. The isomers 5 and 6 represent a rare example for a structurally manifested switch between a non-aromatic and an aromatic state induced by an external stimulus, in this case the complexation of the counter cation.

Chemistry – A European Journal published new progress about Aromaticity. 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Application In Synthesis of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Arikawa, Shinobu; Shimizu, Akihiro; Shintani, Ryo published the artcile< Azoniadibenzo[a,j]phenalenide: A Polycyclic Zwitterion with Singlet Biradical Character>, Electric Literature of 576-83-0, the main research area is azoniadibenzo phenalenide zwitterion singlet triplet biradical crystal structure; aromaticity; density-functional calculations; polycycles; radicals; zwitterions.

A polycyclic zwitterion, azoniadibenzo[a,j]phenalenide, having a singlet biradical character, was synthesized and isolated for the first time. The neg. charge was found to be delocalized over the periphery of the main core of the zwitterion and the pos. charge was localized near the nitrogen atom. Its singlet biradical character was confirmed by a small HOMO-LUMO energy gap with their spatial overlap, and observation of thermally excited triplet species together with DFT calculations

Angewandte Chemie, International Edition published new progress about Atropisomerization. 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Electric Literature of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary