Palladium on Carbon‐Catalyzed Cross‐Coupling using Triarylbismuths

Abstract

Abstract Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na 3 PO 4 ⋅12 H 2 O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N ‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐ n ‐buthylammonium fluoride trihydrate (TBAF⋅3 H 2 O) in which the palladium metals were hardly leached from the catalyst into the reaction media.