Maashi Hussain A, Husayni Abdulrahman H, M Kharou, Reid Michael E, Harnedy James, Herneman Ethan C, Pera-Titus Marc, Morrill Louis C
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom.
Department of Chemistry, College of Science, University of Bisha, Bisha 61922, Saudi Arabia.
Org Lett. 2024 Oct 25;26(42):9051-9055. doi: 10.1021/acs.orglett.4c03091. Epub 2024 Oct 21.
Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C(sp)-rich heterocycles. The reaction proceeds the mesolytic cleavage of anodically generated aromatic radical cations and the trapping of formed carbocation intermediates with internal nucleophiles. The method has been demonstrated across various arylalcohol substrates to access a diverse range of C(sp)-rich heterocycles including tetrahydrofuran, tetrahydropyran, and pyrrolidine scaffolds (26 examples). The electrochemical method was demonstrated on a 5 mmol scale single pass continuous flow, which utilized lower supporting electrolyte concentration and exhibited increased productivity in relation to the batch process.
在此，我们报道了一种用于合成富含C(sp)杂环的电化学解构功能化方法。该反应通过阳极产生的芳基自由基阳离子的均裂裂解以及内部亲核试剂对形成的碳正离子中间体的捕获来进行。该方法已在各种芳基醇底物上得到验证，可用于合成多种富含C(sp)的杂环，包括四氢呋喃、四氢吡喃和吡咯烷骨架（26个实例）。该电化学方法在5 mmol规模下单程连续流中得到了验证，其使用较低的支持电解质浓度，并且相对于间歇过程表现出更高的生产率。
