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

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2223 - 2227

Published: May 14, 2024

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

Language: Английский

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Assembly of Diverse Allenes via Activator-Free Palladium-Catalyzed Regioselective γ-Arylation of Propargylamines with Boronic Acids

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

Controlling the reaction selectivity to achieve a precision synthesis is constant concern for chemists. Here, we report palladium-catalyzed deaminative coupling of propargylamines with arylboronic acids generate allene skeletons. Importantly, this approach allows regioselective γ-arylation unactivated propargyl tertiary amines access various allenes in absence amino-activating reagents. We present wide range and boronic demonstrate synthetic application target products construct valuable compounds.

Language: Английский

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Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Compared with the well-developed cyclization of functionalized propargylamines, use unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted via a DBU-mediated intramolecular cycloaddition N-alkyl propargylamines. This reaction employs dihydropyrrole intermediates, followed by oxidation produce in presence 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, broad substrate scope, high atom economy, selectivity, and simple operation are also advantages this protocol.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 31, 2024

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

Language: Английский

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Synthesis of oxazolines through a Pd-catalyzed alkyne-enabled C N activation of oxazolidines

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 134, P. 154882 - 154882

Published: Dec. 9, 2023

Language: Английский

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Facile synthesis of propargylamines by metal-free doubly decarboxylative coupling

RSC Sustainability, Journal Year: 2024, Volume and Issue: 2(9), P. 2626 - 2631

Published: Jan. 1, 2024

A sustainable and catalyst-free strategy has been developed for the synthesis of propargylamines by a three-component doubly decarboxylative coupling reaction.

Language: Английский

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A novel propiolate-enabled deaminative hiyama coupling of aryl silanes and propargylamines

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 569, P. 114553 - 114553

Published: Sept. 19, 2024

Language: Английский

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

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

Highly regioselective and efficient synthesis of trisubstituted allenes with palladium catalysts via deaminative coupling reaction among tertiary propargylamines arylsiloxanes which were activated in situ using Et 3 N·3HF has been developed.

Language: Английский

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Synthesis of Oxazolines Through a Pd-Catalyzed Alkyne-Enabled C-N Activation of Oxazolidines

Published: Jan. 1, 2023

Strategies that enable selective C-N bond activation of tertiary amines provide one the cornerstones modern organic synthesis. Here we describe a palladium-catalyzed cleavage N-propargyl 1,3-oxazolidines, providing an efficient approach to diverse range oxazolines in good excellent yields. The reaction proceeds through domino process alkyne-enabled 1,5-hydrogen transfer/C-N activation. In this way, two kinds oxazoline skeleton tolerates wide variety functional groups were formed.

Language: Английский

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