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钯催化的二级α-溴代丙酰苯胺的分子内环化合成 3-取代的 2-氧吲哚

Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides palladium-catalyzed intramolecular cyclization.

机构信息

College of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007, P. R. China.

State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. China.

出版信息

Org Biomol Chem. 2022 May 4;20(17):3589-3597. doi: 10.1039/d2ob00480a.

DOI:10.1039/d2ob00480a
PMID:35420109
Abstract

In contrast to aromatic halides, coupling reactions involving oxidative addition of alkyl halides, especially secondary or tertiary halides, to transition metals tend to be more challenging. Herein a palladium-catalyzed intramolecular cyclization of α-bromo-propionanilides has been developed, delivering a series of 3-substituted 2-oxindoles in high yields. The method features easy to prepare starting materials, broad substrate scope and excellent functional group tolerance. A detailed mechanistic investigation has been performed.

摘要

与芳香卤代烃相比,涉及烷基卤化物(特别是仲卤化物或叔卤化物)向过渡金属进行氧化加成的偶联反应往往更具挑战性。在此,我们开发了一种钯催化的α-溴代丙酰苯胺的分子内环化反应,以高产率得到一系列 3-取代的 2-氧吲哚。该方法具有原料易得、底物适用范围广和官能团容忍性好的特点。我们还进行了详细的机理研究。

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