Month: October 2022

The author of 《A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2》 were Jiang, Ying; Sun, Bing; Fang, Wan-Yin; Qin, Hua-Li. And the article was published in European Journal of Organic Chemistry in 2019. SDS of cas: 1194-02-1 The author mentioned the following in the article:

Primary (benzylic) alcs. underwent transition-metal-free one-pot cascade process with SO2F2, K2CO3, and NH2OH·HCl in DMSO to yield nitriles without introducing an addnl. carbon atom. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1SDS of cas: 1194-02-1)

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.SDS of cas: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines》 was written by Gudun, Kristina A.; Slamova, Ainur; Hayrapetyan, Davit; Khalimon, Andrey Y.. Product Details of 1194-02-1 And the article was included in Chemistry – A European Journal in 2020. The article conveys some information:

The com. available and bench-stable Co(acac)2/dpephos system was employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which reacted in-situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Product Details of 1194-02-1)

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.Product Details of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fung, Alfred. K. K.; Yu, Li-Juan; Sherburn, Michael S.; Coote, Michelle L. published their research in Journal of Organic Chemistry in 2021. The article was titled 《Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling》.SDS of cas: 17201-43-3 The article contains the following contents:

A simple nonphotochem. procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N’,N”,N”-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3SDS of cas: 17201-43-3)

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.SDS of cas: 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bortnikov, Evgeniy O.; Semenov, Sergey N. published their research in Journal of Organic Chemistry in 2021. The article was titled 《Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling》.Reference of 4-Bromobenzonitrile The article contains the following contents:

The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to a.c. (AC) through electron transfer steps that occur periodically at the same electrode. AC-assisted Ni-catalyzed amination, etherification, and esterification of aromatic bromides showed higher yields and selectivity compared to that observed in the control experiments with d.c. Our mechanistic studies suggested the importance of both reduction and oxidation processes in the maintenance of the AC-assisted catalytic reactions. As described in presented examples, the AC assistance should be well-suited for catalytic cycles involving reductive elimination or oxidative addition as a limiting step.4-Bromobenzonitrile(cas: 623-00-7Reference of 4-Bromobenzonitrile) was used in this study.

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Reference of 4-Bromobenzonitrile It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Shi, Xinzhe; Zhang, Jian; Roisnel, Thierry; Soule, Jean-Francois; Doucet, Henri published their research in European Journal of Organic Chemistry in 2021. The article was titled 《Palladium-Catalyzed Direct Diarylation of 2-Benzyl-1,2,3-triazole: a Simple Access to 4-Aryl- or 4,5-Diaryl-2-benzyl-1,2,3-triazoles and Phenanthro[9,10-d][1,2,3]triazoles》.HPLC of Formula: 2042-37-7 The article contains the following contents:

The reactivity of 2-benzyl-1,2,3-triazole in palladium-catalyzed direct arylation was studied. The reaction conditions for the selective synthesis of 2-benzyl-4-aryl-1,2,3-triazoles in moderate to high yields using phosphine-free Pd(OAc)2 catalyst and inexpensive KOAc base have been found. Then, from these 4-aryl-1,2,3-triazoles, the palladium-catalyzed C-H bond functionalization of the C5-position allowed the synthesis of the corresponding 4,5-diarylated 2-benzyl-1,2,3-triazoles. This selective 4,5-diarylation of 2-benzyl-1,2,3-triazole was successfully applied for the straightforward building of the π-extended polycyclic heteroaromatic structures phenanthro[9,10-d][1,2,3]triazoles through Pd-catalyzed C4- and C5-intermol. arylations followed by Pd-catalyzed C-H intramol. arylation. In the experiment, the researchers used 2-Bromobenzonitrile(cas: 2042-37-7HPLC of Formula: 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.HPLC of Formula: 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Luo, Jian; Hu, Bo; Wu, Wenda; Hu, Maowei; Liu, T. Leo published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Nickel-Catalyzed Electrochemical C(sp3)-C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides》.Related Products of 623-00-7 The article contains the following contents:

Reported here is the redox neutral electrochem. C(sp2)-C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2·glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochem. coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochem. C-C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Related Products of 623-00-7)

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Related Products of 623-00-7 It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jaime-Figueroa, Saul; Bond, Michael J.; Vergara, J. Ignacio; Swartzel, Jake C.; Crews, Craig M. published an article in 2021. The article was titled 《Synthesis of Isoquinolones by Sequential Suzuki Coupling of 2-Halobenzonitriles with Vinyl Boronate Followed by Cyclization》, and you may find the article in Journal of Organic Chemistry.Application of 2042-37-7 The information in the text is summarized as follows:

A novel, facile, and expeditious two-step synthesis of series of 3,4-unsubstituted isoquinolin-1(2H)-ones from a Suzuki cross-coupling between 2-halobenzonitriles and com. available vinyl boronate followed by platinum-catalyzed nitrile hydrolysis and cyclization was described. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Application of 2042-37-7)

2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Application of 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Dong; Liu, Zhao-Ran; Ma, Cong; Jiao, Ke-Jin; Sun, Bing; Wei, Lei; Lefranc, Julien; Herbert, Simon; Mei, Tian-Sheng published an article in 2021. The article was titled 《Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis》, and you may find the article in Angewandte Chemie, International Edition.Formula: C7H4BrN The information in the text is summarized as follows:

A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochem. (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C-N bond from the resulting NiIII species at room temperature In the part of experimental materials, we found many familiar compounds, such as 4-Bromobenzonitrile(cas: 623-00-7Formula: C7H4BrN)

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Formula: C7H4BrN It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Sharma, Brijesh M.; Nikam, Arun V.; Lahore, Santosh; Ahn, Gwang-Noh; Kim, Dong-Pyo published an article in Chemistry – A European Journal. The title of the article was 《Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound masked -CN source. Non-toxic and stable OxBA reagent is generated by lithiation-borylation of bromo-oxazole, and the consecutive Suzuki-Miyaura cross-coupling with aryl, vinyl, or acetylenic halides and demasking [4+2]/retro-[4+2] sequence were successfully accomplished to give the desired cyano compounds with reasonably good yields in a four-step flow manner. A unique feature of this cyanation protocol in flow enables to cyanate a variety of sp2 and sp carbons to produce a broad spectrum of aryl acetonitrile. It is envisaged that the OxBA based cyanation would replace existing unstable and toxic approaches as well as non-toxic cyanation using two different sources of “”C”” and “”N”” to incorporate the -CN group. In the experiment, the researchers used many compounds, for example, 2-Bromobenzonitrile(cas: 2042-37-7Name: 2-Bromobenzonitrile)

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.Name: 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Zeynizadeh, Behzad; Mousavi, Hossein; Mohammad Aminzadeh, Farkhondeh published an article in Journal of Molecular Structure. The title of the article was 《A hassle-free and cost-effective transfer hydrogenation strategy for the chemoselective reduction of arylnitriles to primary amines through in situ-generated nickel (II) dihydride intermediate in water》.Application In Synthesis of 4-Fluorobenzonitrile The author mentioned the following in the article:

A new, simple, efficient, inexpensive, and chemoselective transfer hydrogenation strategy was introduced for the straightforward reduction of arylnitriles to corresponding primary amines using sodium borohydride (NaBH4) and nickel acetate tetrahydrate (Ni(OAc)2•4H2O) through in situ-generated nickel (II) dihydride intermediate in the water medium at 50°. The presented methodol. featured moderate reaction conditions, nickel boride (Ni2B)-free trajectory, good-to-excellent yields of the products, relatively short reaction times, satisfactory chemoselectivity, and did not involve the use of toxic organic solvent and also any base or ligand. In the experiment, the researchers used 4-Fluorobenzonitrile(cas: 1194-02-1Application In Synthesis of 4-Fluorobenzonitrile)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Application In Synthesis of 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts