Intramolecular palladium-catalyzed alkene carboalkynylation

TETRAHEDRON

卷:71

Article

Nicolai, Stefano¹  Swallow, Peter¹  Waser, Jerome¹ 

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, CH-1015 Lausanne, Switzerland

关键词: Catalysis;    Alkynes;    Alkenes;    Multi-functionalization;    Carbocycles;   

DOI  :  10.1016/j.tet.2015.06.030

来源: Elsevier

【 摘 要 】

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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