Separation of “Light Fluorous” Reagents and Catalysts by Fluorous Solid-Phase Extraction: Synthesis and Study of a Family of Triarylphosphines Bearing Linear and Branched Fluorous Tags
- 1 December 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (26) , 8866-8873
- https://doi.org/10.1021/jo000464f
Abstract
Practical syntheses of new triarylphosphines bearing both linear and branched fluorous tags (Rf) are reported. The phosphines have one, two, or all three aryl rings bearing fluorous tags: (Ph)3-nP(C6H4(CH2)mRf)n. Fluorous−organic partition coefficients have been measured and the retention properties of both the phosphines and the derived phosphine oxides on fluorous reverse phase silica have been studied. While applications relying on liquid−liquid extractive separations of these phosphines may be limited to those bearing three fluorous chains, the technique of solid phase extraction should be broadly applicable to phosphines, phosphine oxides, and derived metal complexes. A parallel platinum-catalyzed allylation of aldehydes with fluorous allyl stannanes illustrates the usefulness of the new fluorous ligands in small-scale synthesis.Keywords
This publication has 36 references indexed in Scilit:
- The rhodium catalysed hydrogenation of styrene in the fluorous biphaseJournal of Fluorine Chemistry, 1999
- Parallel synthesis with fluorous reagents and reactantsMedicinal Research Reviews, 1999
- Fluorous biphasic hydrogenation of 1-alkenes using novel fluorous derivatives of Wilkinson's catalystJournal of Molecular Catalysis A: Chemical, 1999
- Perfluorocarbon-soluble catalysts and reagents and the application of FBS (fluorous biphase system) to organic synthesisJournal of Fluorine Chemistry, 1999
- Reactions involving fluoride ion. Part 44.1 Synthesis and chemistry of aromatics with bulky perfluoroalkyl substituentsJournal of the Chemical Society, Perkin Transactions 1, 1999
- Platinum group metal complexes of a bis(diphenylphosphino)ethane ligand containing perfluoroalkyl ponytailsJ. Chem. Soc., Dalton Trans., 1998
- Platinum group metal complexes of arylphosphine ligands containing perfluoroalkyl ponytails; crystal structures of [RhCl2(η5-C5Me5){P(C6H4C6F13-4)3}] and cis- and trans-[PtCl2{P(C6H4C6F13-4)3}2]J. Chem. Soc., Dalton Trans., 1998
- Palladium‐Catalyzed Cross‐Coupling of Organozinc Bromides with Aryl Iodides in Perfluorinated SolventsAngewandte Chemie International Edition in English, 1997
- Fluorous-phase soluble rhodium complexes: X-ray structure of [RhCl(CO)(P(C2H4C6F13)3 )2]Chemical Communications, 1997
- Phosphorus(III) ligands with fluorous ponytailsJournal of the Chemical Society, Perkin Transactions 1, 1997