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由交替极性驱动的可扩展电化学脱羧烯基化反应

Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity.

作者信息

Garrido-Castro Alberto F, Hioki Yuta, Kusumoto Yoshifumi, Hayashi Kyohei, Griffin Jeremy, Harper Kaid C, Kawamata Yu, Baran Phil S

机构信息

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093, Zürich, Switzerland.

出版信息

Angew Chem Int Ed Engl. 2023 Oct 16;62(42):e202309157. doi: 10.1002/anie.202309157. Epub 2023 Sep 13.

DOI:10.1002/anie.202309157
PMID:37656907
Abstract

A mild, scalable (kg) metal-free electrochemical decarboxylation of alkyl carboxylic acids to olefins is disclosed. Numerous applications are presented wherein this transformation can simplify alkene synthesis and provide alternative synthetic access to valuable olefins from simple carboxylic acid feedstocks. This robust method relies on alternating polarity to maintain the quality of the electrode surface and local pH, providing a deeper understanding of the Hofer-Moest process with unprecedented chemoselectivity.

摘要

公开了一种温和、可扩展(千克级)的无金属电化学方法,可将烷基羧酸脱羧转化为烯烃。文中展示了许多应用实例,该转化过程能够简化烯烃合成,并提供从简单羧酸原料制备有价值烯烃的替代合成途径。这种可靠的方法依靠交替极性来维持电极表面质量和局部pH值,以前所未有的化学选择性对霍费尔-莫斯特反应过程有了更深入的理解。

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