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Nickel-Catalyzed Carbofluoroalkylation of 1,3-Enynes to Access Structurally Diverse Fluoroalkylated Allenes.

Angewandte Chemie 2019 Februrary 18
A nickel-catalyzed 1,4-carbofluoroalkylation of 1,3-enynes to access structurally diverse fluoroalkylated allenes has been established. This method has demonstrated high catalytic reactivity, mild conditions, broad substrates scope and excellent functional group tolerance. The key to success is the use of nickel catalyst to generate different kinds of fluoroalkyl radicals from readily available and structurally diverse fluoroalkyl halides to access 1,4-difunctionalization of 1,3-enynes via a radical relay. This strategy provides facile synthesis of structurally diverse multi-substituted allenes, and offers a solution for batch production of various fluorinated bioactive molecules for drug discovery via further transformations.

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