Intramolecular palladium-catalyzed alkene carboalkynylation. Issue 35 (2nd September 2015)

• Record Type: Journal Article
• Authors: Nicolai, Stefano; Swallow, Peter; Waser, Jerome
• Is Part Of: Tetrahedron. Volume 71:Issue 35(2015)
• Page Start: 5959
• Page End: 5964
• Publication Date: 2015-09-02
• Subjects: Catalysis -- Alkynes -- Alkenes -- Multi-functionalization -- Carbocycles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.06.030
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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 SP 3 –SP C–C bond. The reaction therefore combines ring formation with the introduction of a versatile triple bond for further functionalization. Graphical abstract: