Elsevier

Tetrahedron Letters

Volume 42, Issue 49, 3 December 2001, Pages 8673-8675
Tetrahedron Letters

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

https://doi.org/10.1016/S0040-4039(01)01810-XGet rights and content

Abstract

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.

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Acknowledgements

We thank Leeds University, GlaxoSmithKline, the EU and EPSRC for support.

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