Synthesis of heterocycles via sequential Pd/Ru-catalysed allene insertion–nucleophile incorporation–olefin metathesis

A novel sequential palladium/ruthenium-catalysed three-component process is described involving allenylation of aryl/heteroaryl iodides to generate (π-allyl) palladium species which are intercepted by nitrogen nucleophiles to afford 1,6- and 1,7-dienes. Subsequent ring-closing metathesis affords N-h...

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Bibliographic Details
Published in:Tetrahedron letters 2001-12, Vol.42 (49), p.8673-8675
Main Authors: Dondas, H.Ali, Balme, Genevieve, Clique, Blandine, Grigg, Ronald, Hodgeson, Anne, Morris, James, Sridharan, Visuvanathar
Format: Article
Language:English
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Summary:A novel sequential palladium/ruthenium-catalysed three-component process is described involving allenylation of aryl/heteroaryl iodides to generate (π-allyl) palladium species which are intercepted by nitrogen nucleophiles to afford 1,6- and 1,7-dienes. Subsequent ring-closing metathesis affords N-heterocycles in good yield. A three-component Pd(0)-catalysed cascade followed by ring-closing metathesis using a modified Grubbs catalyst proceeds in good overall yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01810-X