MacDiarmid Institute for Advanced Materials and Nanotechnology, Department of Chemistry, University of Otago, Union Place, Dunedin 9016, New Zealand.
J Org Chem. 2020 Mar 20;85(6):4574-4580. doi: 10.1021/acs.joc.0c00128. Epub 2020 Mar 3.
The three-component reaction between a resorcinol, 1,3-dimethoxybenzene, and an alkyl aldehyde (R = C-C) along with BF·OEt affords a -symmetric resorcin[4]arene tetraether in one step; in most cases, the single isomer can be precipitated from the reaction mixture in moderate to excellent yields (up to 89%). The reaction is tolerant of 2-substituted resorcinols (R' = OH, Cl, Br, Me), allowing a third type of functionality to be regioselectively incorporated during the macrocyclization.
间苯二酚、1,3-二甲氧基苯和烷基醛(R = C-C)的三组分反应与 BF·OEt 一起提供一步法合成 -对称的间苯[4]芳烃四醚;在大多数情况下,单一异构体可以从反应混合物中以中等至优异的产率(高达 89%)沉淀出来。该反应可以容忍 2-取代的间苯二酚(R' = OH、Cl、Br、Me),允许在大环化过程中选择性地引入第三类型的官能团。