Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls

Michael G Organ; Selçuk Calimsiz; Mahmoud Sayah; Ka Hou Hoi; Alan J Lough

doi:10.1002/anie.200805661

Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls

Angew Chem Int Ed Engl. 2009;48(13):2383-7. doi: 10.1002/anie.200805661.

Authors

Michael G Organ¹, Selçuk Calimsiz, Mahmoud Sayah, Ka Hou Hoi, Alan J Lough

Affiliation

¹ Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada.

PMID: 19226587
DOI: 10.1002/anie.200805661

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.