Related Experiment Video
Updated: May 4, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Alcohol-Directed Carboamination of Conjugated Enynes
Helena Solé-Àvila1,2, Duncan K Brownsey1,2, Hugo Senelle1
1Laboratory of Catalysis and Organic Synthesis, Institute of Chemistry and Chemical Engineering, École Polytechnique Fédérale de Lausanne, Lausanne, Switzerland.
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.
Related Concept Videos
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

