Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases
Top Cited Papers
Open Access
- 9 September 2010
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 2 (1), 57-68
- https://doi.org/10.1039/c0sc00330a
Abstract
We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C–N cross-coupling reactions to date. Often low catalyst loadings and short reaction times can be used with functionalized aryl and heteroaryl coupling partners. The reactions are highly robust and can be set up and performed without the use of a glovebox. These catalysts should find wide application in the synthesis of complex molecules including pharmaceuticals, natural products and functional materials.Keywords
This publication has 81 references indexed in Scilit:
- An improved synthesis of N-aryl and N-heteroaryl substituted homopiperazines—from conventional thermal conditions to scaling-up using microwave heatingTetrahedron, 2009
- An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling FactorsJournal of the American Chemical Society, 2009
- A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl ChloridesJournal of the American Chemical Society, 2008
- Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl HalidesAccounts of Chemical Research, 2008
- Biaryl Phosphane Ligands in Palladium‐Catalyzed AminationAngewandte Chemie International Edition, 2008
- A New Class of Easily Activated Palladium Precatalysts for Facile C−N Cross-Coupling Reactions and the Low Temperature Oxidative Addition of Aryl ChloridesJournal of the American Chemical Society, 2008
- Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity RelationshipsJournal of the American Chemical Society, 2008
- Hole-transporting hydrazonesChemical Society Reviews, 2008
- Lewis Acid Acceleration of C−N Bond-Forming Reductive Elimination from Heteroarylpalladium Complexes and Catalytic Amidation of Heteroaryl BromidesJournal of the American Chemical Society, 2007
- Application of a New Bicyclic Triaminophosphine Ligand in Pd-Catalyzed Buchwald−Hartwig Amination Reactions of Aryl Chlorides, Bromides, and IodidesThe Journal of Organic Chemistry, 2003