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