芳乙炔基MIDA硼酸酯的串联环异构化/铃木偶联反应
Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.
作者信息
Chan Julian M W, Amarante Giovanni W, Toste F Dean
机构信息
Department of Chemistry, University of California, Berkeley, California 94720, United States.
出版信息
Tetrahedron. 2011 Jun 17;67(24):4306-4312. doi: 10.1016/j.tet.2011.04.011.
Abstract
A tandem gold-catalyzed cycloisomerization/Suzuki cross coupling sequence involving arylethynyl-N-methyliminodiacetic acid boronates is described. Combining the mildness of homogeneous gold catalysis with the versatility of N-methyliminodiacetic acid (MIDA) boronates, this tandem two-step method enables the rapid assembly of various aryl-substituted heterocycles without having to isolate or purify any heterocyclic MIDA boronate intermediates. Another major advantage of this method is that a wide range of heterocycles bearing different aryl groups may be made from a single MIDA boronate alkyne precursor.
摘要
本文描述了一种串联金催化的环异构化/铃木交叉偶联反应序列，该反应涉及芳基乙炔基-N-甲基亚氨基二乙酸硼酸酯。将均相金催化的温和性与N-甲基亚氨基二乙酸（MIDA）硼酸酯的多功能性相结合，这种串联两步法能够快速组装各种芳基取代的杂环，而无需分离或纯化任何杂环MIDA硼酸酯中间体。该方法的另一个主要优点是，可以从单一的MIDA硼酸酯炔烃前体合成带有不同芳基的多种杂环。
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本文引用的文献
1
Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes.通过未活化烯烃的分子内氨基金化反应制备烷基金配合物。
Chem Sci. 2010 Aug 1;1(2). doi: 10.1039/C0SC00255K.
2
Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.与MIDA硼酸酯的迭代交叉偶联：迈向小分子合成的通用平台
Aldrichimica Acta. 2009;42(1):17-27.
3
Gold-catalyzed carbon-heteroatom bond-forming reactions.金催化的碳-杂原子成键反应。
Chem Rev. 2011 Mar 9;111(3):1657-712. doi: 10.1021/cr100414u.
4
A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.一种基于反应活性驱动的金催化有机反应发现与开发方法。
Synlett. 2010 Mar 1;2010(5):675-691. doi: 10.1055/s-0029-1219369.
5
Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds.金催化芳烃和杂芳烃与 C-C 多重键的修饰。
Chem Soc Rev. 2011 Mar;40(3):1358-67. doi: 10.1039/c0cs00041h. Epub 2010 Nov 22.
6
A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling.一种通过迭代交叉偶联生成立体化学复杂多烯骨架的简单通用平台。
Angew Chem Int Ed Engl. 2010 Nov 15;49(47):8860-3. doi: 10.1002/anie.201004911.
7
Selective synthesis of either isoindole- or isoindoline-1-carboxylic acid esters by Pd(0)-catalyzed enolate arylation.通过 Pd(0)催化的烯醇化物芳基化反应选择性合成异吲哚-1-羧酸酯或异吲哚啉-1-羧酸酯。
J Org Chem. 2010 Sep 17;75(18):6267-70. doi: 10.1021/jo101054j.
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