Tetrabutylammonium 2-Pyridyltriolborate Salts for Suzuki–Miyaura Cross-Coupling Reactions with Aryl Chlorides
- 16 August 2013
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (17) , 4308-4311
Abstract
Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH2CH2OH (20 mol %) in anhydrous DMF without bases.Keywords
This publication has 61 references indexed in Scilit:
- Boronic Acids2011
- Cross-coupling Reactions of Organoboranes: An Easy Method for C–C BondingChemistry Letters, 2011
- Versatile tools in the construction of substituted 2,2′-bipyridines—cross-coupling reactions with tin, zinc and boron compoundsChemical Society Reviews, 2008
- Applications of and alternatives to π-electron-deficient azine organometallics in metal catalyzed cross-coupling reactionsChemical Society Reviews, 2007
- The Synthesis and Applications of Heterocyclic Boronic AcidsSynthesis, 2003
- In situ formation and reaction of 2-pyridylboronic estersTetrahedron Letters, 2003
- Cross-coupling reaction of organoboron compounds via base-assisted transmetalation to palladium(II) complexesJournal of Organometallic Chemistry, 2002
- Organoboron Compounds2002
- Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)–tricyclohexylphosphine complexesTetrahedron, 2001
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995