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
The Journal of Organic Chemistry2004Vol. 69(22), pp. 7635–7639
Citations Over TimeTop 10% of 2004 papers
T. Brenstrum, D.A. Gerristma, George M. Adjabeng, Christopher S. Frampton, James F. Britten, Alan Robertson, James McNulty, Alfredo Capretta
Abstract
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 beta-hydrogens with either boronic acids or alkylboranes.
Related Papers
- → Visible-Light-Driven Reductive Carboarylation of Styrenes with CO 2 and Aryl Halides(2020)276 cited
- → Fast and Easy Halide Exchangein Aryl Halides(2003)11 cited
- → Phosphine-substituted carbonyl halide complexes of chromium and molybdenum(1968)9 cited
- → Palladium-Catalyzed Cyanomethylation of Aryl Halides(2011)
- → ChemInform Abstract: CONVENIENT SYNTHESIS OF ARYL HALIDES FROM ARYLAMINES VIA TREATMENT OF 1‐ARYL‐3,3‐DIALKYLTRIAZENES WITH TRIMETHYLSILYL HALIDES(1982)