A highly efficient metal-free hydrocarbonylation of alkynes with propargylamines and water

Xie, Yujuan; Huang, Liliang; Qi, Yayu; Hu, Junduo; Song, Liangliang; Feng, Huangdi

doi:10.1039/d1gc04487g

Green Chem.

2022

DOI: 10.1039/d1gc04487g

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A highly efficient metal-free hydrocarbonylation of alkynes with propargylamines and water

Yujuan Xie

Liliang Huang

Yayu Qi

et al.

Abstract: Metal-catalyzed hydrocarbofunctionalizations of alkynes or alkenes are well established. In contrast, metal-free strategies have few precedents. We report herein a multicomponent reaction that generates functionalized 1,4-dicarbonyl motifs via formal hydrocarbonylation...

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Cited by 13 publications

References 79 publications

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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Feng,

Xie,

Huang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAllenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties of organic compounds make allenes a desirable choice in various applications. Here, we report a facile method for the atom‐economical synthesis of propargyl allenylamines via an underdeveloped [2,3]‐sigmatropic rearrangement. Our strategy employs easily accessible propargylamines as starting materials, which are first converted into propargyl ammonium salts, followed by a base‐promoted [2,3]‐sigmatropic rearrangement. This one‐pot, two‐step reaction proceeds in the absence of transition metals, displays a very broad scope, and does not require the introduction of the electron‐withdrawing group into the starting materials.

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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Feng,

Xie,

Huang

et al. 2024

Chin. J. Chem.

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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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Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones

Zhou

Huang²,

Xie³

et al. 2023

Molecular Catalysis

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A highly efficient metal-free hydrocarbonylation of alkynes with propargylamines and water

Abstract: Metal-catalyzed hydrocarbofunctionalizations of alkynes or alkenes are well established. In contrast, metal-free strategies have few precedents. We report herein a multicomponent reaction that generates functionalized 1,4-dicarbonyl motifs via formal hydrocarbonylation...

Cited by 13 publications

References 79 publications

Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

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

Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones

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