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

Zhou, Pengyu; Huang, Liliang; Xie, Yujuan; Ma, Gaoxiang; Feng, Huangdi

doi:10.1016/j.mcat.2022.112808

Cited by 5 publications

References 45 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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Precision Propargylic Substitution Reaction: Pd-Catalyzed Suzuki–Miyaura Coupling of Nonactivated Propargylamines with Boronic Acids

Sun,

Zhao,

Wang

et al. 2024

J. Org. Chem.

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Palladium-catalyzed Suzuki−Miyaura cross-coupling is an efficient approach for C−C bond construction. Here we report a deaminative Suzuki−Miyaura reaction to achieve chemo-and regioselectivity in the cross-coupling of nonactivated propargylamines with boronic acids, in which methyl propiolate is introduced to promote the cleavage of the C−N bond to form the C−C bond. This method features a wide range of substrates, good functional group tolerance, and ease of operation, providing an alternative approach to accessing valuable propargylated aromatic compounds.

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Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes

Liao,

Yi,

You

et al. 2025

Org. Chem. Front.

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

Cited by 5 publications

References 45 publications

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

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

Precision Propargylic Substitution Reaction: Pd-Catalyzed Suzuki–Miyaura Coupling of Nonactivated Propargylamines with Boronic Acids

Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes

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