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  • Title: Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls.
    Author: Organ MG, Calimsiz S, Sayah M, Hoi KH, Lough AJ.
    Journal: Angew Chem Int Ed Engl; 2009; 48(13):2383-7. PubMed ID: 19226587.
    Abstract:
    Incredible Bulk: A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were formed from unreactive aryl chlorides using the isopentyl-substituted catalyst at temperatures ranging from 65 degrees C to room temperature. The cyclopentyl-substituted catalyst was virtually inactive, demonstrating that "flexible bulk" is essential to promote these transformations.
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