Category: 401-78-5

Kim, Ji Hye; Constantin, Timothee; Simonetti, Marco; Llaveria, Josep; Sheikh, Nadeem S.; Leonori, Daniele published the artcile< A radical approach for the selective C-H borylation of azines>, HPLC of Formula: 401-78-5, the main research area is borylation azine radical addition approach aminborane reagent; radical addition free energy azine borylation; crystal structure borylated azine boraneylmethylquinoline trimethylamine complex; mol structure borylated azine boraneylmethylquinoline trimethylamine complex.

B functional groups are often introduced in place of aromatic C-H bonds to expedite small-mol. diversification through coupling of mol. fragments1-3. Current approaches based on transition-metal-catalyzed activation of C-H bonds are effective for the borylation of many (hetero)aromatic derivatives4,5 but show narrow applicability to azines (N-containing aromatic heterocycles), which are key components of many pharmaceutical and agrochem. products6. Here the authors report an azine borylation strategy using stable and inexpensive amine-borane7 reagents. Photocatalysis converts these low-mol.-weight materials into highly reactive boryl radicals8 that undergo efficient addition to azine building blocks. This reactivity provides a mechanistically alternative tactic for sp2 C-B bond assembly, where the elementary steps of transition-metal-mediated C-H bond activation and reductive elimination from azine-organometallic intermediates are replaced by a direct, Minisci9-style, radical addition The strongly nucleophilic character of the amine-boryl radicals enables predictable and site-selective C-B bond formation by targeting the azine’s most activated position, including the challenging sites adjacent to the basic N atom. This approach enables access to aromatic sites that elude current strategies based on C-H bond activation, and led to borylated materials that would otherwise be difficult to prepare The authors have applied this process to the introduction of amine-borane functionalities to complex and industrially relevant products. The diversification of the borylated azine products by mainstream cross-coupling technologies establishes aromatic amino-boranes as a powerful class of building blocks for chem. synthesis.

Nature (London, United Kingdom) published new progress about Addition reaction catalysts (tetra(carbazolyl)dicyanobenzene). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, HPLC of Formula: 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Panigrahi, Adyasha; Whitaker, Daniel; Vitorica-Yrezabal, Inigo J.; Larrosa, Igor published the artcile< Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides>, SDS of cas: 401-78-5, the main research area is biaryl preparation; fluoroarene chromium tricarbonyl complex bromoarene arylation silver palladium catalyst.

Diverse C-H functionalizations catalyzed by Pd employ Ag(I) salts added as halide abstractors or oxidants. Recent reports have shown that Ag can also perform the crucial C-H activation step in several of these functionalizations. However, all of these processes are limited by the wasteful requirement for (super)stoichiometric Ag(I) salts. Herein, we report the development of a Ag/Pd cocatalyzed direct arylation of (fluoroarene) chromium tricarbonyl complexes with bromoarenes. The small organic salt, NMe4OC(CF3)3, added as a halide abstractor, enables the use of a catalytic amount of Ag, reversing the rapid precipitation of AgBr. We have shown through H/D scrambling and kinetic studies that a (PR3)Ag-alkoxide is responsible for C-H activation, a departure from previous studies with Ag carboxylates. Furthermore, the construction of biaryls directly from the simple arene is achieved via a one-pot chromium tricarbonyl complexation/C-H arylation/decomplexation sequence using (pyrene)Cr(CO)3 as a Cr(CO)3 donor.

ACS Catalysis published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, SDS of cas: 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yang, Qiang; Sane, Neeraj; Klosowski, Daniel; Lee, Melissa; Rosenthal, Tay; Wang, Nick X.; Wiensch, Eric published the artcile< Mizoroki-Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards>, Product Details of C7H4BrF3, the main research area is bromobenzene styrene palladium catalyst diastereoselective Mizoroki Heck coupling safety; stilbene preparation.

The potential safety hazards associated with the Mizoroki-Heck cross-coupling of bromobenzenes with styrenes were evaluated. The heat output from the reaction in various solvents was comparable in a variety of solvents; however, the rate of reaction was significantly faster in the presence of water. Thermal stability evaluation of the postreaction mixtures in DMSO and 3:1 DMSO/water by differential scanning calorimetry indicated that the onset temperatures of thermal decomposition were significantly lower than that of neat DMSO. Evaluation of the substrate scope revealed that the substitution pattern on the bromobenzene did not affect the heat output. The reaction rate of electron-deficient bromobenzenes was slower than that of the electron-rich bromobenzenes. In general, substituted styrenes afforded similar magnitudes of exotherms; however, the reaction rate of bromobenzene with 2-methylstyrene was significantly slower than the other studied styrenes. The predicted heat of reaction using the d. functional theory method, B3LYP, was in good agreement with the exptl. data. Such excellent agreement suggests that this calculation method can be used as a preliminary tool to predict heat of reaction and avoid exothermic reaction conditions. In many of the studied cases, the maximum temperature of a synthesis reaction was considerably higher than the solvent b.p. and thermal decomposition onset temperatures when the reaction was performed in DMSO or 3:1 DMSO/water. It is crucial to understand the thermal stability of the reaction mixture to design the process accordingly and ensure the reaction temperature is maintained below the onset temperature of decomposition to avoid potential runaway reactions.

Organic Process Research & Development published new progress about Bromobenzenes Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Product Details of C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tlahuext-Aca, Adrian; Lee, Sarah Yunmi; Sakamoto, Shu; Hartwig, John F. published the artcile< Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis>, Quality Control of 401-78-5, the main research area is arene aryl bromide synergistic palladium silver catalyst regioselective arylation; biaryl preparation; C–H activation; aryl bromides; direct arylation; palladium and silver catalysts; synergistic catalysis.

The direct, catalytic arylation of simple arenes in small excess with aryl bromides was disclosed. The developed method did not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.

ACS Catalysis published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Quality Control of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mondal, Totan; Dutta, Sayan; De, Sriman; Koley, Debasis published the artcile< Computational Exploration of Mechanistic Avenues in C-H Activation Assisted Pd-Catalyzed Carbonylative Coupling>, Product Details of C7H4BrF3, the main research area is bond activation palladium catalyzed carbonylative coupling aryl bromide polyfluoroarene.

The detailed mechanism of the intermol. Pd-catalyzed carbonylative coupling reaction between aryl bromides and polyfluoroarenes relying on C(sp2)-H activation was investigated using state-of-the-art computational methods (SMD-B3LYP-D3(BJ)/BS2//B3LYP-D3/BS1). The mechanism unveils the necessary and important roles of a slight excess of carbon monoxide: acting as a ligand in the active catalyst state, participating as a reactant in the carbonylation process, and accelerating the final reductive elimination event. Importantly, the desired carbonylative coupling route follows the rate-limiting C-H activation process via the concerted metalation-deprotonation pathway, which is slightly more feasible than the decarboxylative route leading to byproduct formation by 1.2 kcal/mol. The analyses of the free energies indicate that the choice of base has a significant effect on the reaction mechanism and its energetics. The Cs2CO3 base guides the reaction toward the coupling route, whereas carbonate bases such as K2CO3 and Na2CO3 switch toward an undesired decarboxylative path. However, K3PO4 significantly reduces the C-H activation barrier over the decarboxylation reaction barrier and can act as a potential alternative base. The positional influence of a methoxy substituent in bromoanisole and different substituent effects in polyfluoroarenes were also considered. Our results show that different substituents impose significant impact on the desired carbonylative product formation energetics. Considering the influence of several ligands leads to the conclusion that other phosphine and N-heterocyclic carbene, such as PnBuAd2 and IMes, can be used as an efficient alternative than the exptl. reported PtBu3 ligand exhibiting a clear preference for C-H activation (ΔΔGLS) by 7.1 and 10.9 kcal/mol, resp. We have also utilized the energetic span model to interpret the exptl. results. Moreover, to elucidate the origin of activation barriers, energy decomposition anal. calculations were accomplished for the critical transition states populating the energy profiles.

Journal of Organic Chemistry published new progress about Aryl bromides Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Product Details of C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Zhi-Yun; Cook, Silas P. published the artcile< Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds>, Quality Control of 401-78-5, the main research area is amidyl oxalate hydroxamic ester aryl halide reductive arylation nickel.

Herein, authors describe a nickel-catalyzed reductive arylation of remote C(sp3)-H bonds with aryl electrophiles. The reaction targets secondary and tertiary C(sp3)-H bonds to deliver all-carbon quaternary centers. The success of this method relies on a novel amidyl radical precursor that tolerates reducing conditions-O-oxalate hydroxamic acid esters.

Organic Letters published new progress about Acid chlorides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Quality Control of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sasmal, Arpan; Bera, Jitendra K.; Doucet, Henri; Soule, Jean-Francois published the artcile< Reactivity of antipyrine and haloantipyrines in Pd-catalyzed C-H bond arylations>, Related Products of 401-78-5, the main research area is aryl dimethyl phenyl pyrazolone green preparation; antipyrine aryl bromide arylation palladium catalyst.

Synthesis of 4-(aryl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one I [Ar = 2-(1-methylpyrrolyl), 4-ClC6H4, 1-naphthyl, etc.;] via Pd-catalyzed direct arylation of antipyrine using Pd(OAc)2 as catalyst associated with KOAc as inexpensive base was reported. In most cases, di-Et carbonate was used a sustainable solvent. The reaction tolerated a wide range of functional groups on the aryl bromide partners (e.g., nitrile, nitro, chloro, fluoro, formyl, acetyl, propionyl, benzoyl, ester, Me, methoxy). In addition, some nitrogen-containing heteroaryl bromides were also efficiently coupled with antipyrine. We also demonstrated that in contrast to 4-bromoantipyrine, 4-iodoantipyrine could be employed as an efficient heteroaryl source in Pd-catalyzed C-H bond arylation of 5-membered ring heteroarenes.

Tetrahedron Letters published new progress about Aryl bromides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Related Products of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ghorbani-Choghamarani, Arash; Taherinia, Zahra published the artcile< Chiral cobalt-peptide metal-organic framework (Co-P-MOF) as an efficient and reusable heterogeneous catalyst for the asymmetric sulfoxidative cross-coupling reaction using poly sulfinylpiperazine>, Electric Literature of 401-78-5, the main research area is cobalt based peptide metal organic framework nanocatalyst preparation; chiral sulfoxide green preparation; aryl halide phenylboronic acid sulfoxidative Suzuki coupling cobalt nanocatalyst.

Chiral cobalt metal-organic framework based on peptide with aspartic acid as building block has been synthesized and characterized by FTIR, TGA, DSC, SEM, TEM, BET and X-ray diffraction anal. The catalytic activity of Co-P-MOFs was applied for synthesis of sulfoxides ArS(O)Ph [Ar = Ph, 2-MeC6H4, 4-ClC6H4, etc.] via asym. sulfoxidative cross-coupling using poly sulfinylpiperazine as a novel sulfoxide transfer reagent. The Co-P-MOF could be recycled several times without loss of activity.

Synthetic Metals published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Electric Literature of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Huang, Shuai Shuai; Zheng, Zhan Jiang; Cui, Yu Ming; Xu, Zheng; Yang, Ke Fang; Xu, Li Wen published the artcile< Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam>, Formula: C7H4BrF3, the main research area is difluoroethoxy trifluoromethyl benzenesulfonyl chloride preparation key building block penoxsulam; bromobenzotrifluoride regioselective lithiation coupling chloroxidn copper catalyst.

A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from com. available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C-O coupling to introduce the difluoroethoxy moiety and chloroxidn. conditions to give the desired sulfonyl chloride.

Synthesis published new progress about Arenesulfonyl chlorides Role: SPN (Synthetic Preparation), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Formula: C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chacon-Huete, Franklin; Lasso, Juan David; Szavay, Paul; Covone, Jason; Forgione, Pat published the artcile< Synthesis of 2,5-diaryl nonsymmetric furans C6-platform chemicals via catalytic conversion of biomass and the formal synthesis of dantrolene>, HPLC of Formula: 401-78-5, the main research area is diarylfuran preparation biomass furancarboxylic acid decarboxylation arylation aryl bromide.

Biomass-derived commodity chem. 5-hydroxymethyl furfural is an underutilized C6-platform chem. derived from cellulose that is ideal to prepare next-generation value-added products. We have developed an efficient synthetic strategy to access 2,5-diaryl nonsym. furans from 5-hydroxymethyl furfural utilizing decarboxylative cross-couplings. A key finding was that the presence of the hydroxymethyl handle enhances the yields of the palladium-catalyzed decarboxylative cross-coupling reaction. The method provides access to a broad-range nonsym. 2,5-diaryl furans where each arene can be systematically introduced as required. Addnl., this green synthetic strategy was employed for a formal synthesis of the muscle relaxant Dantrolene in excellent yields.

Journal of Organic Chemistry published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, HPLC of Formula: 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary