Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Liu, Jiarun; Jia, Kuiyong; Du, Tianxing; Zhao, Changyin; Zhu, Rongxiu; Liu, Xigong

doi:10.1055/s-0039-1691528

Cited by 9 publications

(4 citation statements)

References 2 publications

(4 reference statements)

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“…The Liu group has recently reported a TEMPO oxoammonium salt‐mediated oxidative dearomatization of indoles 56 with aromatic ketones 57 in the presence of H 2 SO 4 (Scheme 23). [31] This metal‐free dearomatization reaction proceeded smoothly and tolerated a broad substrate scope, including a number of indoles and aromatic ketones, leading to the desired 2,2‐disubstituted indolin‐3‐ones 58 in good yields. This method built a novel path for the subsequent research on ketones involving dearomatization.…”

Section: Oxidative Dearomatization Reactionsmentioning

confidence: 90%

Application of Metal‐Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds

Zhong

Feng

et al. 2023

The Chemical Record

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The highly efficient construction of complicated heterocyclic frameworks in an atom‐ and step‐economic manner is still one of the cores of synthetic chemistry. Dearomatization reactions show the unique advantage for the construction of functionalized heterocycles and have attracted widespread attention over the past two decades. The metal‐free approach has proved to be a green and sustainable paradigm for the synthesis of spirocyclic, polycyclic and heterocyclic scaffolds, which are widely present in natural products and bioactive molecules. In this review, the advances in the recent six years (2017–2023) in metal‐free dearomatization reactions are highlighted. Emphasis is placed on developments in the field of organo‐catalyzed dearomatization reactions, oxidative dearomatization reactions, Brønsted acid‐ or base‐promoted dearomatization reactions, photoredox‐catalyzed dearomatization reactions, and electrochemical oxidation dearomatization reactions.

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Section: Oxidative Dearomatization Reactionsmentioning

confidence: 90%

Application of Metal‐Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds

Zhong

Feng

et al. 2023

The Chemical Record

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“…Liu and colleagues (Table 1, R) described a metal-free oxidative dearomatization of indoles with aromatic ketones through the use of TEMPO oxoammonium salt. 21 In the presence of H2SO4, the dearomatization went without a hitch and demonstrated a broad substrate range with respect to both indoles and aromatic ketones, producing the matching 2,2-disubstituted indolin-3-ones in good yields. A completely metal-free catalyst system was created for the selective aerobic oxidation of structurally varied benzylic sp 3 C-H bonds of ethers and alkylarenes.…”

Section: Template For Synopen Thiemementioning

confidence: 99%

Recent Applications of TEMPO in Organic Synthesis and Catalysis

Varala,

Seema

2023

SynOpen

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“…190 Later, Zhu, and Liu et al reported a similar Brønsted acid-mediated similar racemic transformation. 191 3-6-3. Oxidation of furan (Scheme 31)…”

Section: -6-1 Oxidation Of Phenolsmentioning

confidence: 99%

The Utility of Oxoammonium Species in Organic Synthesis: Beyond Alcohol Oxidation

Iwabuchi¹,

Nagasawa²

2022

HETEROCYCLES

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Oxoammonium species are electrophilic chemical species generated via single electron oxidation of nitroxyl radicals. Although this species and its salts are known as useful oxidants and active species for (catalytic) oxidation of alcohols into carbonyl compounds in organic synthesis, the benefits of oxoammonium species for the oxidative transformations of numerous types of substrates apart from alcohols has been reported. This review summarizes the synthetic utility of oxoammonium species under both stoichiometric and catalytic conditions with the exception of alcohol oxidation. CONTENTS 1. Introduction 2. Oxoammonium species 3. Oxoammonium species (salt)-mediated oxidative transformation 3-1. Oxidative esterification/amidation 3-2. Oxidation of amines (imines) 3-3. Oxidation of ethers 3-4. Oxidation of enols: α-Aminooxygenation of carbonyl compounds and further applications 3-5. Oxidation of alkenes 3-6. Oxidation of aromatic compounds 3-7. Oxidation of other substrates 3-8. Oxoammonium species for single electron oxidation 3-9. Oxoammonium species as a Lewis acids Conclusions and outlookThis paper is dedicated to Prof. Somsak Ruchirawat on the occasion of his 80th birthday.

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Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Cited by 9 publications

References 2 publications

Application of Metal‐Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds

Application of Metal‐Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds

Recent Applications of TEMPO in Organic Synthesis and Catalysis

The Utility of Oxoammonium Species in Organic Synthesis: Beyond Alcohol Oxidation

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