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Intramolecular palladium-catalyzed alkene carboalkynylation

Nicolai, Stefano  
•
Swallow, Peter
•
Waser, Jerome  
2015
Tetrahedron

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.

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tetrahedron2015-5959GreenAccess.pdf

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