A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology
The Journal of Organic Chemistry2004Vol. 70(1), pp. 161–168
Citations Over TimeTop 1% of 2004 papers
Riina K. Arvela, Nicholas E. Leadbeater, Michael S. Sangi, Victoria A. Williams, Patricia Granados, Robert D. Singer
Abstract
We present here a reassessment of our transition-metal free Suzuki-type coupling protocol. We believe that, although the reaction can be run without the need for addition of a metal catalyst, palladium contaminants down to a level of 50 ppb found in commercially available sodium carbonate are responsible for the generation of the biaryl rather than, as previously suggested, an alternative non-palladium-mediated pathway. We present a revised methodology for Suzuki couplings using ultralow palladium concentrations for use with aryl and vinyl boronic acids and discuss the effects of the purity of the boronic acid on the reaction.
Related Papers
- → Synthesis of novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines by Suzuki cross-coupling reactions(2006)27 cited
- → Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester(2016)6 cited
- → A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids(2006)16 cited
- → Synthesis of N-aryl trifluoromethylarylketoimines by palladium-catalyzed Suzuki coupling reaction of N-aryltrifluoroacetimidoyl chlorides with aryl boronic acids(2010)12 cited
- → ChemInform Abstract: Synthesis of N‐Aryl Trifluoromethylarylketoimines by Palladium‐Catalyzed Suzuki Coupling Reaction of N‐Aryltrifluoroacetimidoyl Chlorides with Aryl Boronic Acids.(2010)