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一锅法在水相中无外加配体和温和条件下合成 2,3-二取代茚酮衍生物。

One-Pot Synthesis of 2,3-Disubstituted Indanone Derivatives in Water under Exogenous Ligand-Free and Mild Conditions.

机构信息

Institute of Material Physics & Chemistry, College of Science, Nanjing Forestry University, Nanjing 210037, China.

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road Nanjing 211816, P. R. China.

出版信息

J Org Chem. 2022 Jun 17;87(12):7884-7894. doi: 10.1021/acs.joc.2c00544. Epub 2022 May 25.

Abstract

Diverse 2,3-substituted indanones are accessed in an efficient and robust protocol by a rhodium-catalyzed tandem carborhodium/cyclization and intramolecular proton shift pathway. The reaction is compatible with a broad range of functional internal acetylenes, especially for natural and functionalized alkynes derivatives, affording the desired indanones in good to excellent yields. Remarkably, this reaction features very mild and sustainable conditions using water as the sole solvent and without exogenous ligands. Control studies support that indanone is formed through the intramolecular proton transfer process from the key intermediate indenol.

摘要

通过铑催化的串联碳铑化/环化和分子内质子迁移途径,可以有效地、稳健地获得各种 2,3-取代的茚满酮。该反应与广泛的功能内部炔烃兼容,特别是对于天然和功能化的炔烃衍生物,以良好到优异的收率得到所需的茚满酮。值得注意的是,该反应具有非常温和且可持续的条件,仅用水作为唯一溶剂,并且不需要外加配体。控制研究支持茚满酮是通过关键中间体茚醇的分子内质子转移过程形成的。

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