Synthesis of a diverse set of phosphorus ligands on solid support and their screening in the Heck reaction

Representative members from five different families of supported phosphine and phosphinite ligands have been prepared from common templates—polymer-bound aminoalcohols. These include β-aminophosphines, N,β-diphosphinoamines, α,β-diphosphinoamines, β-aminophosphinites and N-phosphino-β-aminophosphinites. Representatives of each family of ligands were complexed with Pd(OAc)₂ and screened in the Heck reaction of iodo- and bromobenzene. While the reaction of iodoarenes is ligand-independent, the reaction of bromoarenes is ligand-sensitive. The rationale for this behavior is suggested. Lead ligands for the reaction of bromoarenes were determined.