216369-76-5Relevant academic research and scientific papers
Palladium-induced intramolecular pyridine-allyl coupling reactions: Formation of N-bridgehead heterocycles with a stable C-N bond
Chengebroyen, Jaganaiden,Grellier, Mary,Pfeffer, Michel
, p. 1563 - 1571 (1998)
In the presence of stoichiometric amounts of bis(acetonitrile)dichloropalladium(II) the ortho-alkenylpyridines 2-but-3′-en-1′-ylpyridine (1), 2-pent-5′-en-1′-ylpyridine (2), 2-hex-5′-en-1′-ylpyridine (3), 2-hept-6′-en-1′-ylpyridine (4) and 2-methyl-6-pent-4′-en-1′-ylpyridine (5) led to a mixture of coordination compounds such as 2-alken-1′-ylpyridine-kN:k2C-dichloropalladium(II) and bis(2-alken-1′-ylpyridine-kN)-dichloropalladium(II) together with 2-pent-4-ene-1′,3′-diylpyridine-kN:k 3C-chloropalladium(II) and 2-hex-4-en-1′,3′-diylpyridine-kN:K3C-chloropalladium(II) in the case of 2 and 3 respectively. The latter were quantitatively demetallated in the presence of an excess of triphenylphosphane to yield tris(triphenylphosphane)palladium(0), 2-vinyl-2,3-dihydroindolizinium chloride and 2-prop-1′-en-1′-yl-2,3-dihydroindolizinium chloride, respectively, by a regioselective addition of the pyridine unit onto the more congested terminal carbon atom of the allyl fragment.
