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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

Zhang, Q and Luo, Z and Curran, DP (2000) 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. Journal of Organic Chemistry, 65 (26). 8866 - 8873. ISSN 0022-3263

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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.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, Q
Luo, Z
Curran, DPcurran@pitt.eduCURRAN
Date: 29 December 2000
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 65
Number: 26
Page Range: 8866 - 8873
DOI or Unique Handle: 10.1021/jo000464f
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Catalysis; Fluorides--chemistry; Indicators and Reagents; Magnetic Resonance Spectroscopy; Phosphines--chemical synthesis; Phosphines--chemistry
PubMed ID: 11149827
Date Deposited: 14 Feb 2014 16:54
Last Modified: 12 Jun 2021 22:56
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/20563

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