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通过阳极氧化两步连续流动合成六元环碘鎓盐

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation.

作者信息

Spils Julian, Wirth Thomas, Nachtsheim Boris J

机构信息

Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, 28359 Bremen, Germany.

School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff CF10 3AT, UK.

出版信息

Beilstein J Org Chem. 2023 Jan 3;19:27-32. doi: 10.3762/bjoc.19.2. eCollection 2023.

Abstract

We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel-Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield.

摘要

我们描述了一种用于生成六元二芳基碘鎓盐的多步连续流动程序。其伴随的可扩展性和原子经济性是对现有间歇方法的重大改进。乙酸苄酯作为高度易得且廉价的起始原料用于此两步程序。酸催化的傅克烷基化反应,随后进行阳极氧化环化反应,以高度依赖底物的产率生成了一组特定的环状碘鎓盐。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ea5c/9830492/2dcd0021c249/Beilstein_J_Org_Chem-19-27-g003.jpg

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