Efficient Suzuki-Miyaura coupling of (hetero)aryl chlorides with thiophene- and furanboronic acids in aqueous n-butanol.
An efficient Suzuki cross-coupling protocol enables the reaction of N-hetero and normal aryl chlorides with thiophene- and furanboronic acids. Coupling is effected in aqueous n-butanol as the solvent in near quantitative yield with a catalyst loading of 0.1-1 mol %. For heterocyclic substrates aqueous catalysis is found to be more efficient than Suzuki coupling under anhydrous conditions. The developed Suzuki coupling procedure utilizes biodegradable solvents and is useful for large scale reactions, as it includes the facile product separation from a biphasic solvent mixture without the need for additional organic solvents during workup.
Fleckenstein
Christoph A
CA
Anorganische Chemie im Zintl-Institut, TU Darmstadt, Petersenstrasse 18, 64287 Darmstadt, Germany.
Plenio
Herbert
H
D020001:1-Butanol / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D017606:Chlorine Compounds / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001897:Boronic Acids; D017606:Chlorine Compounds; D005663:Furans; D008024:Ligands; D012997:Solvents; D013876:Thiophenes; D014867:Water; D020001:1-Butanol; C039281:furan