A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes was written by Le, Chip;Chen, Tiffany Q.;Liang, Tao;Zhang, Patricia;MacMillan, David W. C.. And the article was included in Science (Washington, DC, United States) in 2018.Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:
Transition metal-catalyzed arene functionalization was widely used for mol. synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, this copper oxidative addition problem can be overcome with an aryl radical-capture mechanism, wherein the aryl radical was generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Name: 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. 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. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts