Pd‐PEPPSI‐IPent: An Active, Sterically Demanding Cross‐Coupling Catalyst and Its Application in the Synthesis of Tetra‐Ortho‐Substituted Biaryls
Top Cited Papers
- 10 March 2009
- journal article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 48 (13) , 2383-2387
- https://doi.org/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.Keywords
This publication has 31 references indexed in Scilit:
- Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig ReactionsJournal of the American Chemical Society, 2006
- Active catalysts for the Suzuki coupling: Palladium complexes of tetrahydropyrimid-2-ylidenesJournal of Molecular Catalysis A: Chemical, 2006
- Synthesis of novel (NHC)Pd(acac)Cl complexes (acac=acetylacetonate) and their activity in cross-coupling reactionsTetrahedron, 2005
- Metal‐Catalyzed Cross‐Coupling ReactionsPublished by Wiley ,2004
- Synthesis, Characterization, and Catalytic Activity of N-Heterocyclic Carbene (NHC) Palladacycle ComplexesOrganic Letters, 2003
- Activation and Reactivity of (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes in Cross-Coupling ReactionsOrganometallics, 2002
- Direct Coupling of Oxazolines and N-Heterocyclic Carbenes: A Modular Approach to a New Class of C−N Donor Ligands for Homogeneous CatalysisOrganometallics, 2002
- A Highly Efficient Catalyst for the Telomerization of 1,3-Dienes with Alcohols: First Synthesis of a Monocarbenepalladium(0)-Olefin ComplexAngewandte Chemie International Edition in English, 2002
- Ein hocheffizienter Katalysator für die Telomerisation von 1,3‐Dienen mit Alkoholen: die erste Synthese eines Monocarbenolefinpalladium( 0 )‐KomplexesAngewandte Chemie, 2002
- Unexpected reactivity of two-coordinate palladium–carbene complexes; synthetic and catalytic implicationsChemical Communications, 2001