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钯催化次膦酸酯与醇的烯丙基化/苄基化反应

Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols.

作者信息

Fers-Lidou Anthony, Berger Olivier, Montchamp Jean-Luc

机构信息

Department of Chemistry and Biochemistry, TCU Box 298860, Texas Christian University, Fort Worth, TX 76129, USA.

出版信息

Molecules. 2016 Sep 28;21(10):1295. doi: 10.3390/molecules21101295.

DOI:10.3390/molecules21101295
PMID:27689979
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6273960/
Abstract

The Pd-catalyzed direct alkylation of -phosphinic acids and hypophosphorous acid with allylic/benzylic alcohols has been described previously. Here, the extension of this methodology to -phosphinate esters is presented. The new reaction appears general, although its scope is narrower than with the acids, and its mechanism is likely different. Various alcohols are examined in their reaction with phosphinylidene compounds R¹R²P(O)H.

摘要

钯催化的次膦酸和次磷酸与烯丙基/苄醇的直接烷基化反应此前已有报道。在此,我们展示了该方法对次膦酸酯的拓展。新反应似乎具有通用性,尽管其适用范围比与酸反应时更窄,且其反应机理可能不同。研究了各种醇与亚膦酰基化合物R¹R²P(O)H的反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/6485e3550ed7/molecules-21-01295-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/1c496875474d/molecules-21-01295-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/5555015df3d0/molecules-21-01295-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/c46f01e950d0/molecules-21-01295-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/cfbce6618a8f/molecules-21-01295-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/6485e3550ed7/molecules-21-01295-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/1c496875474d/molecules-21-01295-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/5555015df3d0/molecules-21-01295-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/c46f01e950d0/molecules-21-01295-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/cfbce6618a8f/molecules-21-01295-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0bf6/6273960/6485e3550ed7/molecules-21-01295-sch005.jpg

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本文引用的文献

1
General synthesis of P-stereogenic compounds: the menthyl phosphinate approach.P-手性化合物的一般合成:次膦酸薄荷酯法。
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Green, Palladium-Catalyzed Synthesis of Benzylic H-phosphinates from Hypophosphorous Acid and Benzylic Alcohols.格林,由次磷酸和苄醇通过钯催化合成苄基次膦酸酯
European J Org Chem. 2008 Aug 1;2008(24):4101-4103. doi: 10.1002/ejoc.200800581.
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Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines.通过类卡宾介导的2H-氮杂环丙烷开环反应合成吡啶。
Angew Chem Int Ed Engl. 2013 Feb 18;52(8):2212-6. doi: 10.1002/anie.201209301. Epub 2013 Jan 10.
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Insights into a surprising reaction: the microwave-assisted direct esterification of phosphinic acids.对一个令人惊讶的反应的深入了解:微波辅助膦酸的直接酯化反应。
Org Biomol Chem. 2012 Mar 14;10(10):2011-8. doi: 10.1039/c2ob06972e. Epub 2012 Feb 1.
8
Allylic phosphinates via palladium-catalyzed allylation of H-phosphinic acids with allylic alcohols.通过钯催化次膦酸与烯丙醇的烯丙基化反应制备烯丙基次膦酸酯。
Org Lett. 2008 Mar 20;10(6):1123-6. doi: 10.1021/ol8000415. Epub 2008 Feb 21.
9
Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles: methodology for the synthesis of allylic h-phosphinates.次磷酸化合物与丙二烯、二烯及烯丙基亲电试剂的钯催化反应:烯丙基次膦酸酯的合成方法
J Org Chem. 2008 Mar 21;73(6):2292-301. doi: 10.1021/jo702542a. Epub 2008 Feb 15.
10
Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols.钯催化次磷酸与烯丙醇的脱水烯丙基化反应。
Org Lett. 2006 Aug 31;8(18):4169-71. doi: 10.1021/ol061828e.