title: Polymer-assisted solution-phase (PASP) Suzuki couplings employing an anthracene-tagged palladium catalyst.
abstract: A general method for polymer-assisted solution-phase (PASP) Suzuki reactions employing a combination of anthracene-tagged palladium catalyst and anthracene-tagged boronic acid with a polymer-supported carbonate base is reported. The anthracene-tagged catalyst allows for the easy removal of the Pd catalyst along with the dissociated phosphine ligand and phosphine oxide byproducts by sequestration through a chemoselective Diels-Alder reaction with a maleimide resin. The polymer-supported carbonate base facilitates the removal of excess boronic acid and the borane-containing byproducts present at the end of the coupling reaction. The Suzuki coupling reaction can be efficiently conducted by using combinations of the anthracene-tagged Pd catalyst, polymer-supported carbonate base, and anthracene-tagged boronic acid to yield the desired product in high purity and yield without the use of chromatography.
authors.affiliation: Department of Medicinal and Combinatorial Chemistry, Pharmacia Corporation, 800 North Lindbergh Boulevard, St. Louis, Missouri 63167, USA.
authors.forename: Ping
authors.initials: P
authors.lastname: Lan
authors.forename: Daniela
authors.initials: D
authors.lastname: Berta
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
authors.forename: Michael S
authors.initials: MS
authors.lastname: South
authors.forename: John J
authors.initials: JJ
authors.lastname: Parlow