Intramolecular palladium-catalyzed alkene carboalkynylation

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.


Published in:
Tetrahedron, 71, 35, 5959-5964
Year:
2015
Publisher:
Oxford, Elsevier
ISSN:
0040-4020
Keywords:
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 Record created 2015-09-28, last modified 2018-09-13

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