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α-碘代烯胺酮上的微波辅助铃木-宫浦偶联反应

Microwave-assisted Suzuki-Miyaura couplings on α-iodoenaminones.

作者信息

Wang Xin, Turunen Brandon J, Leighty Matthew W, Georg Gunda I

机构信息

Department of Medicinal Chemistry and Center for Methodology and Library Development, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.

出版信息

Tetrahedron Lett. 2007 Dec 10;48(50):8811-8814. doi: 10.1016/j.tetlet.2007.10.078.

DOI:10.1016/j.tetlet.2007.10.078
PMID:19079569
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2134984/
Abstract

A systematic study of α-iodination and subsequent Suzuki-Miyaura couplings between non-attenuated enaminones and a wide range of aromatic boronic acids is reported. The microwave-assisted variant of this transformation furnished the α-arylenaminones in significantly shorter reaction times and slightly improved yields as compared to conventional heating.

摘要

报道了对未衰减烯胺酮与多种芳基硼酸之间的α-碘化及随后的铃木-宫浦偶联反应的系统研究。与传统加热相比,该转化反应的微波辅助变体能够在显著更短的反应时间内得到α-芳基烯胺酮,产率也略有提高。

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本文引用的文献

1
The alkaloids: chemistry and biology. Preface.生物碱:化学与生物学。前言。
Alkaloids Chem Biol. 2008;65:ix. doi: 10.1016/s1099-4831(07)00010-7.
2
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Chem Commun (Camb). 2006 Dec 14(46):4814-6. doi: 10.1039/b610734f.
3
Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions.哌啶酮的立体选择性合成及其通过有机金属偶联反应的修饰。
Org Biomol Chem. 2007 Jan 21;5(2):349-54. doi: 10.1039/b615113b. Epub 2006 Nov 30.
4
Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.氨基酸衍生的烯胺酮:关于环形成的研究,提供有价值的不对称合成子。
J Am Chem Soc. 2006 Jul 12;128(27):8702-3. doi: 10.1021/ja0609046.
5
Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C.可循环使用的Pd(0)/C催化2-碘环烯酮与芳基硼酸进行实用且高效的铃木-宫浦交叉偶联反应。
J Org Chem. 2005 Oct 14;70(21):8575-8. doi: 10.1021/jo051501b.
6
Controlled microwave heating in modern organic synthesis.现代有机合成中的可控微波加热。
Angew Chem Int Ed Engl. 2004 Nov 26;43(46):6250-84. doi: 10.1002/anie.200400655.
7
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J Org Chem. 1997 Oct 17;62(21):7435-7438. doi: 10.1021/jo9711495.
8
Synthesis of murrayaquinone-A.九里香醌-A的合成。
Chem Pharm Bull (Tokyo). 1994 Jun;42(6):1325-7. doi: 10.1248/cpb.42.1325.