Sequential Pd/Ru-catalysed allenylation/olefin metathesis/1,3-dipolar cycloaddition route to novel heterocycles |
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| Authors: | Ronald Grigg Anne HodgsonJames Morris Visuvanathar Sridharan |
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| Institution: | a Molecular Innovation, Diversity and Automated Synthesis (MIDAS) Centre, School of Chemistry, Leeds University, LS2 9JT, UK
b Process R and D, GlaxoSmithKline, Dartford DA1 5HA, UK |
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| Abstract: | A novel sequential palladium/ruthenium-catalysed four component process is described involving carbonylation of an aryl/heteroaryl iodide followed by allenylation to generate (π-allyl) palladium species which are intercepted by nitrogen nucleophiles to afford 1,6-dienes. Subsequent Ring-Closing Metathesis (RCM) affords C-acyl-N-heterocycles in good yield. These heterocycles proved to be active dipolarophiles in sequential and cascade 1,3-dipolar cycloaddition reactions (1,3-DC) as exemplified by reactions with nitrones and azomethine ylides. |
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