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未活化烯烃的无金属电化学二羟基化反应

Metal-free electrochemical dihydroxylation of unactivated alkenes.

作者信息

Liu Min, Feng Tian, Wang Yanwei, Kou Guangsheng, Wang Qiuyan, Wang Qian, Qiu Youai

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.

出版信息

Nat Commun. 2023 Oct 13;14(1):6467. doi: 10.1038/s41467-023-42106-8.

DOI:10.1038/s41467-023-42106-8
PMID:37833286
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10575955/
Abstract

Herein, a metal-free electrochemical dihydroxylation of unactivated alkenes is described. The transformation proceeds smoothly under mild conditions with a broad range of unactivated alkenes, providing valuable and versatile dihydroxylated products in moderate to good yields without the addition of costly transition metals and stoichiometric amounts of chemical oxidants. Moreover, this method can be applied to a range of natural products and pharmaceutical derivatives, further demonstrating its synthetic utility. Mechanistic studies have revealed that iodohydrin and epoxide intermediate are formed during the reaction process.

摘要

在此,描述了一种未活化烯烃的无金属电化学二羟基化反应。该转化反应在温和条件下顺利进行,适用于多种未活化烯烃,无需添加昂贵的过渡金属和化学计量的化学氧化剂,就能以中等至良好的产率提供有价值且用途广泛的二羟基化产物。此外,该方法可应用于一系列天然产物和药物衍生物,进一步证明了其合成实用性。机理研究表明,反应过程中会形成碘代醇和环氧化物中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/56005399482c/41467_2023_42106_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/815ecfc0812e/41467_2023_42106_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/14c76b1ecc7a/41467_2023_42106_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/a9e96d51d42c/41467_2023_42106_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/56005399482c/41467_2023_42106_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/815ecfc0812e/41467_2023_42106_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/14c76b1ecc7a/41467_2023_42106_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/a9e96d51d42c/41467_2023_42106_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab58/10575955/56005399482c/41467_2023_42106_Fig4_HTML.jpg

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Electrochemical synthesis of vicinal azidoacetamides.邻位叠氮基乙酰胺的电化学合成
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Olefin Dihydroxylation Using Nitroarenes as Photoresponsive Oxidants.使用硝基芳烃作为光响应氧化剂的烯烃双羟基化。
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Tailoring photocatalysts to modulate oxidative potential of anilides enhances para-selective electrochemical hydroxylation.定制光催化剂以调节酰苯胺的氧化电位可增强对位选择性电化学羟基化反应。
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