2-氨基吲哚合成中的连续金属催化C-N键形成
A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.
作者信息
Yao Pei-Yuan, Zhang Yu, Hsung Richard P, Zhao Kang
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
出版信息
Org Lett. 2008 Oct 2;10(19):4275-8. doi: 10.1021/ol801711p. Epub 2008 Aug 28.
Abstract
A sequential metal-catalyzed C-N bond formation employing ortho-haloaryl acetylenic bromides is described. The initial amidation is highly selective for C (sp)-N bond formation, leading to o-haloaryl-substituted ynamides that can be useful building blocks, while the overall sequence provides a facile construction of 2-amido-indoles.
摘要
描述了一种使用邻卤芳基乙炔基溴化物的顺序金属催化的C-N键形成反应。初始酰胺化反应对C(sp)-N键的形成具有高度选择性，生成可作为有用构建单元的邻卤芳基取代的烯炔酰胺，而整个反应序列为2-氨基吲哚的简便构建提供了方法。
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1
Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism.过渡金属催化由芳基卤化物和三氟甲磺酸芳基酯合成芳胺和芳基醚：范围与机理
Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2046-2067. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L.
2
3
A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.通过使用烯炔酰胺的衣笠反应对手性α-氨基-β-内酰胺进行高度立体选择性合成。
Org Lett. 2008 Aug 21;10(16):3477-9. doi: 10.1021/ol801257j. Epub 2008 Jul 10.
4
Synthesis of functionalized oxazolones by a sequence of Cu(II)- and Au(I)-catalyzed transformations.通过一系列铜（II）和金（I）催化的转化反应合成功能化恶唑酮
Org Lett. 2008 Mar 6;10(5):925-8. doi: 10.1021/ol703077g. Epub 2008 Feb 2.
5
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Org Lett. 2008 Feb 21;10(4):661-3. doi: 10.1021/ol703083k. Epub 2008 Jan 17.
6
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J Am Chem Soc. 2008 Jan 23;130(3):833-5. doi: 10.1021/ja077406x. Epub 2008 Jan 1.
7
A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles.偕二卤代烯烃的高选择性串联交叉偶联反应用于模块化、高效合成高度官能化的吲哚。
J Org Chem. 2008 Jan 18;73(2):538-49. doi: 10.1021/jo701987r. Epub 2007 Dec 22.
8
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Chem Commun (Camb). 2007 Jun 21(23):2420-2. doi: 10.1039/b701040k.
9
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10
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Org Lett. 2007 Jul 19;9(15):2955-8. doi: 10.1021/ol071370w. Epub 2007 Jun 27.
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