Month: October 2022

The author of 《Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases》 were Xu, Jessica; Liu, Richard Y.; Yeung, Charles S.; Buchwald, Stephen L.. And the article was published in ACS Catalysis in 2019. Safety of 2-(3-Bromophenyl)acetonitrile The author mentioned the following in the article:

The Pd-catalyzed cross-coupling of thiols with aromatic electrophiles is a reliable method for the synthesis of aryl thioethers, which are important compounds for pharmaceutical and agricultural applications. Since thiols and thiolates strongly bind late transition metals, previous research has focused on catalysts supported by chelating, bisphosphine ligands, which were considered less likely to be displaced during the course of the reaction. We show that, by using monophosphine ligands instead, more effective catalysis can be achieved. Notably, compared to previous methods, this increased reactivity allows for the use of much lower reaction temperature, soluble bases, and base-sensitive substrates. In contrast to conventional wisdom, our mechanistic data suggest that the extent of displacement of phosphine ligands by thiols is, first, not correlated with the ligand bulk or thiol nucleophilicity and, second, not predictive of the effectiveness of a given ligand in combination with palladium. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Safety of 2-(3-Bromophenyl)acetonitrile) was used in this study.

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Safety of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid》 were Islas, Rosa E.; Garcia, Juventino J.. And the article was published in ChemCatChem in 2019. Reference of 4-Fluorobenzonitrile The author mentioned the following in the article:

In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using com. available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction’s selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Reference of 4-Fluorobenzonitrile)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Reference of 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Regioregularity and Electron Deficiency Control of Unsymmetric Diketopyrrolopyrrole Copolymers for Organic Photovoltaics》 were Aoshima, Kenta; Nomura, Mayuka; Saeki, Akinori. And the article was published in ACS Omega in 2019. Formula: C7H3BrFN The author mentioned the following in the article:

Manipulating the electron deficiency and controlling the regioregularity of π-conjugated polymers are important for the fine-tuning of their electronic and electrochem. properties to make them suitable for an organic solar cell. Here, we report such a mol. design of unsym. diketopyrrolopyrrole (DPP) based copolymers with different aromatic side units of either thiophene (Th), pyridine (Py), or fluorobenzene (FBz). The unsym. electron acceptors of Th-DPP-Py and Th-DPP-FBz were polymerized with the electron donor of two-dimensional benzobisthiophene (BDT-Th), affording two regiorandom DPP copolymers. They exhibited contrasting MO levels and bulk heterojunction morphol. in methanofullerene-blended films, leading to power conversion efficiencies of 3.75 and 0.18%, resp. We further synthesized a regioregular DPP copolymer via sandwiching the centrosym. BDT-Th unit by two Th-DPP-Py units in an axisym. manner. The extensive characterization through morphol. observation, X-ray diffraction, and space-charge-limited current mobilities highlight the case-dependent pos./neg. effects of regioregularity and electron deficiency control. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Formula: C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Catalytic Conversion of N-Heteroaromatics to Functionalized Arylamines by Merging Hydrogen Transfer and Selective Coupling》 was published in ACS Catalysis in 2020. These research results belong to Tan, Zhenda; Ci, Chenggang; Yang, Jian; Wu, Yang; Cao, Liang; Jiang, Huanfeng; Zhang, Min. Safety of 4-Cyanobenzyl bromide The article mentions the following:

A ruthenium-catalyzed deconstruction of N-heteroaromatics to functionalized arylamines with 2-aminoaryl methanols via hydrogen transfer and selective coupling was reported. The reaction was achieved via sequential functionalization of the β and α-sites of the initially formed N-heteroarenium salts followed by a C-N cleavage, proceeding with the striking features of broad substrate scope, excellent functional groups tolerance, high chemoselectivity and atom-efficiency, and applicable for streamline synthesis of some biomedical mols. The strategy utilized will pave the avenues for further development of catalytic transformations of inert organo-systems to functional frameworks. In the experimental materials used by the author, we found 4-Cyanobenzyl bromide(cas: 17201-43-3Safety of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.Safety of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation》 was written by Tan, Zhi-Yu; Wu, Ke-Xin; Huang, Lu-Shan; Wu, Run-Shi; Du, Zheng-Yu; Xu, Da-Zhen. Name: 3-Oxo-3-phenylpropanenitrile And the article was included in Green Chemistry in 2020. The article conveys some information:

The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (mol. oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process. The results came from multiple reactions, including the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Name: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Cooperative Molybdenum-Thiolate Reactivity for Transfer Hydrogenation of Nitriles》 was written by Hou, Shu-Fen; Chen, Jia-Yi; Xue, Minghui; Jia, Mengjing; Zhai, Xiaofang; Liao, Rong-Zhen; Tung, Chen-Ho; Wang, Wenguang. Synthetic Route of C7H4FN And the article was included in ACS Catalysis in 2020. The article conveys some information:

A half-sandwich molybdenum(II) thiolate complex with a η2-MeCN ligand, Cp*Mo(1,2-Ph2PC6H4S)(η2-NCMe), was found to catalyze transfer hydrogenation of nitriles efficiently with ammonia borane (H3N•BH3) at room temperature, producing primary amines. Through molybdenum-thiolate cooperation, the B-H bond of BH3 is cleaved, affording a Mo(II)-H hydride (Cp*Mo(1,2-Ph2PC6H4S)H(BH2)) with the BH2 moiety captured at the S-Mo unit. In the presence of NH3, Cp*Mo(1,2-Ph2PC6H4S)H(BH2) smoothly achieves the catalytic transfer hydrogenation of nitriles. The results came from multiple reactions, including the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Synthetic Route of C7H4FN)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Synthetic Route of C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Upadhyay, Rahul; Kumar, Shashi; Maurya, Sushil K. published their research in ChemCatChem in 2021. The article was titled 《V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls》.HPLC of Formula: 614-16-4 The article contains the following contents:

The versatile application of different functional groups such as alcs. (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions has been reported. The method was successfully applied for the alc. oxidation, oxidative scission of styrenes, and benzylic C-H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30% aqueous), TBHP (70% aqueous), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4HPLC of Formula: 614-16-4)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.HPLC of Formula: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pan, Ming; Shao, Ying-Bo; Zhao, Qun; Li, Xin published an article in 2022. The article was titled 《Asymmetric Synthesis of N-N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations》, and you may find the article in Organic Letters.Reference of 4-Cyanobenzyl bromide The information in the text is summarized as follows:

A wide range of N-N axially chiral quinazolinone derivatives I (R1 = Ph, prop-1-en-2-yl, 3-chlorphenyl, etc.; R2 = Ph, 1-naphthyl, prop-1-ynyl, etc.; R3 = Ph, t-Bu, 3-bromophenyl, etc.; R4 = H, 7-Me, 6-I, 5-Cl, etc.) were prepared by phase-transfer catalysis in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. D. functional theory calculations provide insight into the mechanism. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3Reference of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.Reference of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Feng, Yunhui; Luo, Hang; Zheng, Wanyao; Matsunaga, Shigeki; Lin, Luqing published an article in 2022. The article was titled 《Light-Promoted Nickel-Catalyzed Aromatic Halogen Exchange》, and you may find the article in ACS Catalysis.Recommanded Product: 2042-37-7 The information in the text is summarized as follows:

Visible-light-induced, single nickel-catalyzed halogen exchange of aromatic halides ArX (Ar = 4-chlorophenyl, naphthalen-1-yl, 1H-indol-7-yl, etc.; X = Cl, Br, I) with the corresponding halide salts such as sodium iodide, tetrabutylammonium bromide, benzyltriethylammonium chloride under mild conditions was reported. Varieties of aryl iodides ArI, bromides ArBr, and chlorides ArCl can smoothly undergo aromatic Finkelstein or retro-Finkelstein reactions with good functional group tolerance. Exptl., mechanistic studies showed that excited-state NiII complexes for facile reductive elimination to form carbon-halide bonds were involved in the process of Finkelstein and retro-Finkelstein reactions. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Recommanded Product: 2042-37-7)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Recommanded Product: 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Visible-Light-Induced Dehydrohalogenative Coupling for Intramolecular α-Alkenylation: A Way to Build Seven- and Eight-Membered Rings》 was written by Xu, Dawen; Li, Han; Pan, Guangxing; Huang, Pan; Oberkofler, Jens; Reich, Robert M.; Kuhn, Fritz E.; Guo, Hao. Quality Control of 4-Cyanobenzyl bromideThis research focused onvisible light dehydrohalogenative coupling photocycloaddition diene. The article conveys some information:

A visible-light-induced intramol. α-alkenylation has been developed via metal-free dehydrohalogenative C(sp2)-C(sp2) coupling reaction to afford seven- and eight-membered rings. Extensive mechanistic studies prove that this reaction proceeds through a [2+2]-photocycloaddition, elimination, and retro-[2+2]-photocycloaddition process, with cyclobutane and cyclobutene being involved as key intermediates. This transformation is broadly applicable and highly stereoselective, yielding exclusively cyclic (1Z,3Z)-1,3-diene via photochem. allowed disrotation. This protocol excavates new applications of [2 + 2]-photocycloadditions, which may find their way in future olefin-olefin coupling reactions and medium-sized ring synthesis. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Quality Control of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Quality Control of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts