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Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compounds as nucleophiles and an alkynyl bromide as an electrophile, the reaction gives access to cyclopentanes in 44-93% yield and one example of cyclohexane in 31% yield with simultaneous formation of a SP3-SP C-C bond. The reaction therefore combines ring formation with the introduction of a versatile triple bond for further functionalization. (C) 2015 Elsevier Ltd. All rights reserved.
Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ...