Reductive 3-Silylation of Benzofuran Derivatives via Coupling Reaction with Chlorotrialkylsilane was written by Zheng, Suhua;Zhang, Tianyuan;Maekawa, Hirofumi. And the article was included in Journal of Organic Chemistry in 2020.Product Details of 1646-27-1 This article mentions the following:
Reductive silylation of benzofurans with an electron-withdrawing group by a magnesium metal and the subsequent oxidative rearomatization by DDQ gave the selective formation of less reported 3-silylated benzofurans in moderate to good yields under mild reaction conditions with wide substituent scope. The silyl group introduced on the five-membered ring by the reductive coupling could survive with no elimination throughout the oxidation process. The silylated heteroaromatic skeleton is useful as an intermediate in organic synthesis, and its practical utility was also demonstrated by several transformation reactions. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Product Details of 1646-27-1).
Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Product Details of 1646-27-1
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem