Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(II)/norbornene catalysis for aniline synthesis was written by Chen, Shuqing;Wang, Peng;Cheng, Hong-Gang;Yang, Chihui;Zhou, Qianghui. And the article was included in Chemical Science in 2019.Computed Properties of C12H16BBrO2 This article mentions the following:
A palladium(II)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines was reported. The method was scalable, robust (tolerance of air and moisture), phosphine ligand-free and compatible with a wide range of functionalities. These practical features made this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines which often cannot be prepared via other transition-metal-catalyzed aminations were readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides was demonstrated. Preliminary deuterium-labeling studies revealed a redox-neutral ipso-protonation mechanism of this process, which will surely inspire the future development of this field. Overall, the exceptionally broad scope (47 examples) and reliability of this procedure, together with the wide availability of pinacol arylborates made this chem. a valuable addition to the existing methods for aniline synthesis. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Computed Properties of C12H16BBrO2).
2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Computed Properties of C12H16BBrO2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts