Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts

J Org Chem. 2008 Oct 3;73(19):7731-4. doi: 10.1021/jo8014819. Epub 2008 Sep 11.

Abstract

A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates. Catalyst loading can be reduced to 0.2 mol % for coupling of nonactivated aryl tosylate. A challenging example for room temperature coupling is realized. The scope of this highly active Pd/L2 system can be extended to other boron nucleophiles, including trifluoroborate salts and boronate esters. The ligand structural comparisons toward the reactivity in tosylate couplings are also described.