ISSN:
1434-1948
Keywords:
ortho-Alkenylpyridines
;
C-H Activation
;
Palladium
;
Pyridine-allyl coupling
;
Indolizinium derivatives
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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-ĸN:ĸ2C-dichloropalladium(II) and bis(2-alken-1′-ylpyridine-ĸN)-dichloropalladium(II) together with 2-pent-4-ene-1′,3′-diylpyridine-ĸN:ĸ3C-chloropalladium(II) and 2-hex-4-en-1′,3′-diylpyridine-ĸN:ĸ3C-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.
Type of Medium:
Electronic Resource
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