Palladium-Induced Intramolecular Pyridine-Allyl Coupling Reactions: Formation of N-Bridgehead Heterocycles with a Stable C–N Bond

✍ Scribed by Jaganaiden Chengebroyen; Mary Grellier; Michel Pfeffer

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 280 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-1948
• DOI: 10.1002/(sici)1099-0682(199810)1998:10<1563::aid-ejic1563>3.0.co;2-p

✦ Synopsis

In the presence of stoichiometric amounts of bis(ace-1Ј,3Ј-diylpyridine-κN:κ 3 C-chloropalladium(II) in the case of 2 and 3 respectively. The latter were quantitatively tonitrile)dichloropalladium(II) the ortho-alkenylpyridines 2but-3Ј-en-1Ј-ylpyridine (1), 2-pent-5Ј-en-1Ј-ylpyridine (2), 2-demetallated in the presence of an excess of triphenylphosphane to yield tris(triphenylphosphane)palladium(0), 2-hex-5Ј-en-1Ј-ylpyridine (3), 2-hept-6Ј-en-1Ј-ylpyridine (4) and 2-methyl-6-pent-4Ј-en-1Ј-ylpyridine (5) led to a mixture vinyl-2,3-dihydroindolizinium chloride and 2-prop-1Ј-en-1Јyl-2,3-dihydroindolizinium chloride, respectively, by a of coordination compounds such as 2-alken-1Ј-ylpyridine-κN:κ 2 C-dichloropalladium(II) and bis(2-alken-1Ј-ylpyridine-regioselective addition of the pyridine unit onto the more congested terminal carbon atom of the allyl fragment. κN)-dichloropalladium(II) together with 2-pent-4-ene-1Ј,3Јdiylpyridine-κN:κ 3 C-chloropalladium(II) and 2-hex-4-en-