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  • Title: An efficient low-temperature Stille-Migita cross-coupling reaction for heteroaromatic compounds by Pd-PEPPSI-IPent.
    Author: Dowlut M, Mallik D, Organ MG.
    Journal: Chemistry; 2010 Apr 12; 16(14):4279-83. PubMed ID: 20209529.
    Abstract:
    The reactivity of Pd-PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization, and Initiation) precatalysts in the Stille-Migita cross-coupling reaction between heteroaryl stannanes and aryl or heteroaryl halides was evaluated. In general, Pd-PEPPSI-IPent (IPent=diisopentylphenylimidazolium derivative) demonstrated high efficiency over a variety of challenging aryl or heteroaryl halides with thiophene-, furan-, pyrrole-, and thiazole-based organostannanes when compared with Pd-PEPPSI-IPr (IPr=diisopropylphenylimidazolium 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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