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Phosphaadamantanes as Ligands for Palladium Catalyzed Cross-Coupling Chemistry:  Library Synthesis, Characterization, and Screening in the Suzuki Coupling of Alkyl Halides and Tosylates Containing β-Hydrogens with Boronic Acids and Alkylboranes

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posted on 29.10.2004, 00:00 by Tim Brenstrum, David A. Gerristma, George M. Adjabeng, Christopher S. Frampton, James Britten, Alan J. Robertson, James McNulty, Alfredo Capretta
A 15-member library of phosphaadamantane ligands has been prepared via P-arylation of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane. Screening of this tertiary phosphine collection has allowed for the rapid determination of the most suitable ligand, specifically 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane, for facilitating Suzuki-type couplings of alkyl halides or tosylates containing β-hydrogens with either boronic acids or alkylboranes.