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May 7, 2026Angewandte Chemie0 citationsOpen Access

Alcohol‐Directed Carboamination of Conjugated Enynes

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HSHelena Solé‐ÀvilaInstitute of Catalysis and PetrochemistryDBDuncan K. BrownseyInstitute of Catalysis and PetrochemistryHSHugo SenelleÉcole Polytechnique Fédérale de Lausanne

Key Points

  • The aim is to develop a novel method for synthesizing functionalized allenic amines using carboamination techniques.
  • Pd-catalyzed carboamination of conjugated enynes
  • 1,4-coupling of anilines and aryl triflates with enynes
  • Utilization of a free alcohol as a directing group
  • Sequential carboamination to produce multifunctionalized heterocycles
  • Facilitated synthesis of functionalized allenic amines
  • Demonstrated cyclization to dihydropyrans
  • Enabled hydroamination and tandem carboamination sequences
  • Produced 3-pyrroline heterocycles through dual C-N bond formation with distinct aryl triflates

Abstract

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.

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Cite This Study

Solé‐Àvila et al. (2026) studied this question.

synapsesocial.com/papers/69fbe2b3164b5133a91a2277https://doi.org/10.1002/ange.6963888
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