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α-和β-芳基乙烯基醚的选择性方法。

Selective Approaches to α- and β-Arylated Vinyl Ethers.

机构信息

Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), University of La Rioja, Madre de Dios 53, 26006, Logroño, Spain.

出版信息

Angew Chem Int Ed Engl. 2022 Jan 3;61(1):e202109801. doi: 10.1002/anie.202109801. Epub 2021 Nov 23.

DOI:10.1002/anie.202109801
PMID:34758166
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9299197/
Abstract

We developed simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.

摘要

我们开发了简单高效的钯催化区域选择性α-和β-芳基化反应的方法,适用于结构多样的乙烯基醚。这两种催化方法在相对温和的反应条件下进行,适用于广泛的底物范围,包括更复杂的化合物,提供芳基化的葡萄糖或异色烯。反应不需要大量试剂过量,具有很高的经济性,限制了废物的产生。计算研究(DFT)的结果提供了对决定所研究反应明显区域选择性的关键因素的深入了解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7493/9299197/93fc4b4d0be7/ANIE-61-0-g001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7493/9299197/5715e7d481dc/ANIE-61-0-g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7493/9299197/646e099c9494/ANIE-61-0-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7493/9299197/93fc4b4d0be7/ANIE-61-0-g001.jpg

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Confirmation of the Revised Structure of Samoquasine A and a Proposed Structural Revision of Cherimoline.确认萨莫夸辛 A 的修订结构和对切里莫林的建议结构修订。
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