Rentería-Gómez Ángel, Guerrero Macayla, Ramirez-Lopez Mireya, Gutierrez Osvaldo
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
Org Lett. 2023 Oct 13;25(40):7440-7445. doi: 10.1021/acs.orglett.3c03059. Epub 2023 Sep 29.
Fluoroalkylated compounds are important entities in agrochemicals, pharmaceuticals, and materials. The catalytic dicarbofunctionalization of alkenes represents a powerful strategy for the rapid construction and diversification of compounds. In this vein, multicomponent cross-coupling reactions (MC-CCR) can provide an efficient synthetic route to build molecular complexity. In this work, we report the first iron-catalyzed three-component fluoroalkylarylation of enamides via selective formation and trapping of α-amide radicals under mild conditions and fast reaction times. The reaction tolerates a variety of commercially available aryl Grignard reagents and fluoroalkyl halides. Finally, the use of a removable phthalimido group provides an efficient strategy to prepare highly valuable γ-difluoroalkylated amines.
氟烷基化化合物是农用化学品、药物和材料中的重要物质。烯烃的催化双碳官能化是化合物快速构建和多样化的有力策略。在此背景下，多组分交叉偶联反应（MC-CCR）可为构建分子复杂性提供一条高效的合成路线。在本工作中，我们报道了首例铁催化的烯酰胺三组分氟烷基芳基化反应，该反应在温和条件下和较短反应时间内通过选择性形成并捕获α-酰胺自由基实现。该反应能耐受多种市售芳基格氏试剂和氟代烷基卤化物。最后，使用可去除的邻苯二甲酰亚氨基基团提供了一种制备高价值γ-二氟烷基化胺的有效策略。
