通过 SEM 保护的吡咯的铃木-宫浦偶联反应高效合成芳基取代的吡咯。
An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki⁻Miyaura Coupling Reaction of SEM-Protected Pyrroles.
机构信息
College of Life Science and Bio-engineering, Beijing University of Technology, 100 Ping Le Yuan, Chaoyang District, Beijing 100124, China.
State Key Laboratory of Bioactive Substances and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, China.
出版信息
Molecules. 2019 Apr 22;24(8):1594. doi: 10.3390/molecules24081594.
An efficient arylation of SEM-protected pyrroles by the Suzuki-Miyaura coupling reaction has been developed. The reaction can be carried out under mild conditions to provide aryl-substituted pyrroles in moderate to excellent yields. The scope and limitations of the methodology were evaluated, and the reaction was tolerant of a wide range of functionalities. Compared to the reported methods, the protocol has some advantages, such as commercially available materials, no debrominated by-products being formed, and the amine-protecting group being stable under the reaction conditions. The synthetic utility of the product has also been demonstrated, with several common transformations of the aryl-substituted pyrrole product being conducted. This protocol will offer the opportunity to explore other metal-catalyzed cross-coupling reactions employing SEM-protected pyrroles.
已开发出一种通过 Suzuki-Miyaura 偶联反应高效芳基化 SEM 保护吡咯的方法。该反应可以在温和条件下进行，以中等至优异的收率提供芳基取代的吡咯。评估了该方法的范围和局限性，并且该反应对多种官能团具有耐受性。与报道的方法相比，该方案具有一些优点，例如商业上可获得的材料、不形成脱溴副产物和胺保护基在反应条件下稳定。该产品的合成实用性也得到了证明，对芳基取代的吡咯产物进行了几种常见的转化。该方案将为探索其他采用 SEM 保护吡咯的金属催化交叉偶联反应提供机会。
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