Alcohol‐Directed Carboamination of Conjugated Enynes

We report a Pd-catalyzed carboamination of conjugated enynes for the direct synthesis of functionalized allenic amines. The reaction proceeds through a selective 1,4-coupling of anilines and aryl triflates with enynes, utilizing a free alcohol as a native directing group. The obtained allenes undergo versatile transformations, including cyclization to dihydropyrans, hydroamination, and tandem carboamination sequences. Notably, the use of primary anilines enables a second carboamination to generate multifunctionalized 3-pyrroline heterocycles through dual C-N bond formation with two distinct aryl triflates. The transformation represents a novel approach to allene synthesis and heterocycle construction through sequential carboamination events.

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Journal
Angewandte Chemie International Edition
Published
2026-05-02
DOI
https://doi.org/10.1002/anie.6963888
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Alcohol‐Directed Carboamination of Conjugated Enynes

Duncan K. Brownsey, Helena Solé-Àvila, Hugo Senelle, Jerome Waser
Angewandte Chemie International Edition
Catalytic C–H Functionalization Methods
article

Alcohol‐Directed Carboamination of Conjugated Enynes

Duncan K. Brownsey, Helena Solé-Àvila, Hugo Senelle, Jerome Waser
article en

Abstract

We report a Pd-catalyzed carboamination of conjugated enynes for the direct synthesis of functionalized allenic amines. The reaction proceeds through a selective 1,4-coupling of anilines and aryl triflates with enynes, utilizing a free alcohol as a native directing group. The obtained allenes undergo versatile transformations, including cyclization to dihydropyrans, hydroamination, and tandem carboamination sequences. Notably, the use of primary anilines enables a second carboamination to generate multifunctionalized 3-pyrroline heterocycles through dual C-N bond formation with two distinct aryl triflates. The transformation represents a novel approach to allene synthesis and heterocycle construction through sequential carboamination events.

Angewandte Chemie International Edition
Institute of Catalysis and Petrochemistry (RU), École Polytechnique Fédérale de Lausanne (CH)
École Polytechnique Fédérale de Lausanne
Clean water and sanitation
Openalex Percentile: Top 13%
Catalytic C–H Functionalization Methods
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