Palladium-Catalyzed Synthesis of 2,3-Diaryl-N-methylindoles from ortho-Alkynylanilines and Aryl Pinacol Boronic Esters was written by Luo, Yue-Gui;Basha, R. Sidick;Reddy, Daggula Mallikarjuna;Xue, Yong-Jing;Chen, Te-Hsuan;Lee, Chin-Fa. And the article was included in Organic Letters in 2018.Reference of 68716-49-4 This article mentions the following:
A palladium-catalyzed synthesis of 2,3-diaryl-N-methylindoles from o-alkynylanilines and aryl pinacol boronic esters was developed. The system possesses high functional group tolerance and a broad substrate scope with a variety of aryl pinacol boronic esters to provide valuable 2,3-diaryl-N-methylindoles in moderate to good yields. Remarkably, the sequential reaction controlled by iridium-catalyzed C-H borylation or palladium-catalyzed alkynylation followed by the present palladium-catalyzed C3 arylation reaction provided functionalized 2,3-diaryl-N-methylindoles in good yields. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Reference of 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.Reference of 68716-49-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts