Alcohol‐Directed Carboamination of Conjugated Enynes
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.
Article Details
Authors (4)
Helena Solé‐Àvila
Laboratory of Catalysis and Organic Synthesis Institute of Chemistry and Chemical Engineering, École Polytechnique Fédérale de Lausanne Lausanne Switzerland
Duncan K. Brownsey
Laboratory of Catalysis and Organic Synthesis Institute of Chemistry and Chemical Engineering, École Polytechnique Fédérale de Lausanne Lausanne Switzerland
Hugo Senelle
Laboratory of Catalysis and Organic Synthesis Institute of Chemistry and Chemical Engineering, École Polytechnique Fédérale de Lausanne Lausanne Switzerland
Jerome Waser
Laboratory of Catalysis and Organic Synthesis