Selective Synthesis of 2-(Indol-3-Yl)Phenols via Iodine-Catalyzed C3-Arylation of Indoles with Cyclohexanones

IF 4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-01-10 DOI:10.1002/adsc.202401507
Qi Yin, Xinlin Zhou, Chao Zhang, Shanping Chen, Yuxia Li, Guo-Jun Deng
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Abstract

An iodine-catalyzed C3-arylation of indoles with cyclohexanones to selectively synthesize 2-(indol-3-yl)phenols has been described. Mechanism studies indicate that the oxygen atom in 2-(indol-3-yl)phenols is originally from DMSO. This cascade involving dehydration condensation, selective oxygenation, dehydrogenation, and aromatization was achieved in one pot under transition-metal-free conditions.

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碘催化吲哚与环己酮的C3 -芳基化选择性合成2 -(吲哚- 3 -基)苯酚
碘催化吲哚与环己酮的C3芳化反应选择性地合成了2 -(吲哚- 3 -基)苯酚。机理研究表明,2 -(吲哚- 3 -基)酚中的氧原子最初来自二甲基亚砜。该级联反应包括脱水缩合、选择性氧化、脱氢和芳构化,在无过渡金属的条件下在一个锅中完成。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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