首页> 外文期刊>The Journal of Organic Chemistry >Palladium(0)-Catalyzed, Copper(Ⅰ)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon-Carbon Bond Formation for the Functionalization of Heterocycles
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Palladium(0)-Catalyzed, Copper(Ⅰ)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon-Carbon Bond Formation for the Functionalization of Heterocycles

机译:钯(0)催化,铜(Ⅰ)介导的硼酸与环硫酰胺的偶联。用于杂环功能化的选择性碳-碳键形成

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摘要

The palladium-catalyzed cross-coupling of cyclic thioamides with arylboronic acids in the presence of stoichiometric amounts of a copper(Ⅰ) cofactor is described. The desulfitative carbon-carbon cross-coupling protocol is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Successful carbon-carbon cross-coupling is independent of the ring size, aromaticityonaromaticity, the presence of additional heteroatoms, or other functional groups in the starting thioamide structure. Employing controlled microwave irradiation at 100℃, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is the fact that the system can be tuned to an alternative carbon-sulfur cross-coupling pathway by changing to stoichiometric copper(Ⅱ) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to the traditional base-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with boronic acids.
机译:描述了在化学计量的铜(Ⅰ)辅因子存在下,钯催化的环硫酰胺与芳基硼酸的交叉偶联。脱硫碳-碳交叉偶联方案是在中性条件下进行的,可应用于具有嵌入的硫酰胺片段的杂环结构。成功的碳-碳交叉偶联与环的大小,芳香性/非芳香性,起始硫酰胺结构中是否存在其他杂原子或其他官能团无关。通过在100℃下控制微波辐射,大多数交叉偶联可在2小时内完成,并以高收率进行。使用硫代酰胺作为起始原料的一个优点是,可以通过在氧化条件下更改为化学计量的铜(Ⅱ),将系统调节至另一种碳硫交叉偶联途径。两种类型的硫酰胺交叉偶联均与芳基卤化物与硼酸的传统碱催化的铃木-宫浦交叉偶联正交。

著录项

  • 来源
    《The Journal of Organic Chemistry》 |2007年第12期|p.4440-4448|共9页
  • 作者单位

    Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

  • 入库时间 2022-08-18 00:02:20

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