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无溶剂条件下硅胶介导的有机反应。

Silica gel-mediated organic reactions under organic solvent-free conditions.

机构信息

Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.

出版信息

Molecules. 2012 Sep 27;17(10):11469-83. doi: 10.3390/molecules171011469.

DOI:10.3390/molecules171011469
PMID:23018922
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268860/
Abstract

Silica gel was found to be an excellent medium for some useful organic transformations under organic solvent-free conditions, such as (1) the Friedel-Crafts-type nitration of arenes using commercial aqueous 69% nitric acid alone at room temperature, (2) one-pot Wittig-type olefination of aldehydes with activated organic halides in the presence of tributyl- or triphenylphosphine and Hunig's base, and (3) the Morita-Baylis-Hillman reaction of aldehydes with methyl acrylate. After the reactions, the desired products were easily obtained in good to excellent yields through simple manipulation.

摘要

硅胶被发现是一种在无有机溶剂条件下进行某些有用的有机转化的优良介质,例如:(1) 在室温下仅使用商业 69%的硝酸水溶液进行芳基的 Friedel-Crafts 型硝化;(2) 在三丁基或三苯基膦和 Hunig 碱的存在下,用活性有机卤化物一锅法进行 Wittig 型烯丙基化;(3) 用甲基丙烯酸甲酯进行 Morita-Baylis-Hillman 反应。反应后,通过简单的操作,很容易以良好到优异的收率获得所需产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/e521887330b8/molecules-17-11469-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/09d0a052e8c7/molecules-17-11469-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/0adb20272893/molecules-17-11469-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/c59e8f487385/molecules-17-11469-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/e521887330b8/molecules-17-11469-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/09d0a052e8c7/molecules-17-11469-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/0adb20272893/molecules-17-11469-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/c59e8f487385/molecules-17-11469-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b8d/6268860/e521887330b8/molecules-17-11469-g004.jpg

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J Am Chem Soc. 2012 Jun 6;134(22):9225-39. doi: 10.1021/ja300943z. Epub 2012 May 25.
2
The Baylis-Hillman reaction: a novel concept for creativity in chemistry.Baylis-Hillman 反应:化学创造性的新概念。
Chem Soc Rev. 2012 Jan 7;41(1):68-78. doi: 10.1039/c1cs15174f. Epub 2011 Sep 6.
3
Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: ionic liquid based systems for aromatic nitration.
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J Org Chem. 2011 Oct 7;76(19):8088-94. doi: 10.1021/jo201374a. Epub 2011 Sep 13.
4
Chromatography-free Wittig reactions using a bifunctional polymeric reagent.无色谱分离的 Wittig 反应使用双功能高分子试剂。
Org Lett. 2010 Nov 5;12(21):4996-9. doi: 10.1021/ol1021614.
5
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7
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9
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10
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