Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 14, Pages 4279-4283Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903337
Keywords
biaryls cross-coupling; heterocycles; Stille-Migita reaction; palladium
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Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Ontario Research and Development Challenge Fund (ORDCF)
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The reactivity of Pd-PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization, and Initiation) precatalysts in the Stille-Migita crosscoupling reaction between heteroaryl stannanes and aryl or heteroaryl halides was evaluated. In general, Pd PEPPSI-IPent (Went = dnsopentylphenylimidazolium derivative) demonstrated high efficiency over a variety of challenging aryl or heteroaryl halides with thiophene-, furan-, pyrrole-, and thiazole-based oreanoslanntines when compared with Pd-PEPPSI-IPr (IPr = chisopropylphenyhmidazolium derivative). The transformations proceeded at appreciably lower temperatures (30-80 degrees C) than triarylphosphine-based Pd catalysts, improving the scope of this useful carbon-carbon bond-forming process
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