Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65^th birthday

Abstract

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me₂-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd₂(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 Me₂-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

Key words

arylation - oxindoles - Pd catalysis - asymmetric - BI-DIME

• References

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