Category: 68716-49-4

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis was written by Guo, Peng;Wang, Ke;Jin, Wen-Jie;Xie, Hao;Qi, Liangliang;Liu, Xue-Yuan;Shu, Xing-Zhong. And the article was included in Journal of the American Chemical Society in 2021.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Herein, a dynamic kinetic cross-coupling approach for the direct functionalization of alcs were reported. The feasibility of this strategy was demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcs. with (hetero)aryl electrophiles. The reaction proceeded with a broad substrate scope of both coupling partners. The electron-rich, electron-poor and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enabled the direct arylation of benzylic alc. in the presence of various nucleophilic groups, including non-activated primary/secondary/tertiary alcs., phenols, and free indoles. It thus offered a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biol. active mols. and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process was an initial step in the reaction with aryl electrophiles. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Aryl Halides was written by Wang, Xin;Zhu, Ming-Hui;Schuman, David P.;Zhong, Dayou;Wang, Wen-Yan;Wu, Lin-Yang;Liu, Wei;Stoltz, Brian M.;Liu, Wen-Bo. And the article was included in Journal of the American Chemical Society in 2018.HPLC of Formula: 68716-49-4 This article mentions the following:

Herein a general, mild and scalable method for deuterium incorporation by potassium methoxide/hexamethyldisilane-mediated dehalogenation of aryl halides was described. With CD₃CN as a deuterium source, a wide array of heteroarenes prevalent in pharmaceuticals and bearing diverse functional groups are labeled with excellent deuterium incorporation (>60 examples). The ipso-selectivity of this method provides precise access to libraries of deuterated indoles and quinolines. The synthetic utility of our method has been demonstrated by the incorporation of deuterium into complex natural and drug-like compounds In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4HPLC of Formula: 68716-49-4).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.HPLC of Formula: 68716-49-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades was written by Dauncey, Elizabeth M.;Dighe, Shashikant U.;Douglas, James J.;Leonori, Daniele. And the article was included in Chemical Science in 2019.HPLC of Formula: 68716-49-4 This article mentions the following:

A divergent strategy for the remote arylation, vinylation and alkylation of nitriles e.g., I is described. These processes proceed through the photoredox generation of a cyclic iminyl radical and its following ring-opening reaction. The distal nitrile radical is then engaged in nickel-based catalytic cycles to form C-C bonds with aryl bromides ArBr [Ar = 4-(acetyl)phenyl, 2-methylpyridin-4-yl, 1H-1,3-benzodiazol-2-yl, etc.], alkynes RCCH [R = (CH₂)₄CH₃, cyclohexyl, 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propyl, etc.] and alkyl bromides R¹Br [R¹ = 3-phenylpropyl, 4-(1,3-dioxolan-2-yl)butyl, 2-chloroethyl, etc.]. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4HPLC of Formula: 68716-49-4).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.HPLC of Formula: 68716-49-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ni-catalyzed Reductive Deaminative Arylation at sp³ Carbon Centers was written by Martin-Montero, Raul;Yatham, Veera Reddy;Yin, Hongfei;Davies, Jacob;Martin, Ruben. And the article was included in Organic Letters in 2019.Application of 68716-49-4 This article mentions the following:

A Ni-catalyzed reductive deaminative arylation at unactivated sp³ carbon centers is described. This operationally simple and user-friendly protocol exhibits excellent chemoselectivity profile and broad substrate scope, thus complementing existing metal-catalyzed cross-coupling reactions to forge sp³ C-C linkages. These virtues have been assessed in the context of late-stage functionalization, hence providing a strategic advantage to reliably generate structure diversity with amine-containing drugs. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Application of 68716-49-4).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Application of 68716-49-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts