Zheng Suhua, Zhang Tianyuan, Maekawa Hirofumi
Department of Materials Science and Technology, Nagaoka University of Technology, 1603-1 Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan.
J Org Chem. 2020 Nov 6;85(21):13965-13972. doi: 10.1021/acs.joc.0c01995. Epub 2020 Oct 12.
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.
带有吸电子基团的苯并呋喃通过金属镁进行还原硅氢化反应，随后经2,3-二氯-5,6-二氰基对苯醌（DDQ）进行氧化芳构化反应，在温和的反应条件下、在较宽的取代基范围内，以中等至良好的产率选择性地生成了较少报道的3-硅基化苯并呋喃。通过还原偶联反应引入到五元环上的硅基在整个氧化过程中都能保留而不消除。硅基化的杂芳族骨架作为有机合成中的中间体很有用，并且通过几个转化反应也证明了其实际应用价值。
