Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Article abstract of DOI:10.1055/s-0036-1591590

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me ₂ -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd ₂ (dba) ₃ / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me ₂ -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.