Brockmann Mike, Lobbel Jonas, Unterriker Lara, Herges Rainer
Otto Diels-Institute of Organic Chemistry, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany.
Beilstein J Org Chem. 2024 Nov 15;20:2954-2958. doi: 10.3762/bjoc.20.248. eCollection 2024.
In this study, novel fluorinated carboxylic acid esters of the generic structure TfO-CH-(CF) -COOCH ( = 2,4,6, Tf = triflate) were synthesized. The triflates were reacted with 2-hydroxy-3,4,5-trimethoxybenzaldehyde via Williamson ether syntheses. The resulting electron-rich compounds were used as aldehydes in the Rothemund reaction with pyrrole to form ester-substituted porphyrins. After metalation with Ni(acac) and hydrolysis electron-rich porphyrins were obtained, that are equipped with covalently attached long chain acid substituents. The target compounds have potential applications in catalysis, sensing, and materials science. The fluorinated aliphatic carboxylic acids (TfO-CH-(CF) -COOCH) with triflate as leaving group in terminal position are easily accessible and versatile building blocks for attaching long chain acids (p 0-1) to substrates in Williamson ether-type reactions.
在本研究中，合成了通式为TfO-CH-(CF) -COOCH （ = 2,4,6，Tf = 三氟甲磺酸酯）的新型氟化羧酸酯。三氟甲磺酸酯通过威廉姆森醚合成法与2-羟基-3,4,5-三甲氧基苯甲醛反应。所得富电子化合物在与吡咯的罗特蒙德反应中用作醛，以形成酯取代的卟啉。在用Ni(acac)进行金属化和水解后，得到了带有共价连接的长链酸取代基的富电子卟啉。目标化合物在催化、传感和材料科学领域具有潜在应用。末端带有三氟甲磺酸酯作为离去基团的氟化脂肪族羧酸（TfO-CH-(CF) -COOCH）易于获得，是在威廉姆森醚型反应中将长链酸（p 0-1）连接到底物上的通用结构单元。
