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Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines

Curran, DP and Wang, X and Zhang, Q (2005) Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines. Journal of Organic Chemistry, 70 (9). 3716 - 3719. ISSN 0022-3263

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Abstract

(Equation Presented) The relative reactivities of triphenylphosphine (PPh3) and three fluorous triarylphosphines [(p-RF(CH 2)2C6H4)nPPh 3-n, where n = 1-3] have been compared in internal competition experiments. Product ratios were determined by 31P NMR spectroscopy. The four phosphines have about the same reactivities in oxidation, alkylation, and Staudinger reactions and give comparable yields in a preparative Mitsunobu reaction. Previously observed rate and yield differences in Staudinger reactions of the fluorous phosphines are attributed to solubility effects, not reactivity differences. A light fluorous phosphine [(p-C8F17(CH 2)2C6H4PPh2] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4. © 2005 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Wang, X
Zhang, Q
Date: 29 April 2005
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 70
Number: 9
Page Range: 3716 - 3719
DOI or Unique Handle: 10.1021/jo050116j
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Catalysis; Hydrocarbons, Fluorinated--chemistry; Indicators and Reagents; Magnetic Resonance Spectroscopy; Molecular Structure; Phosphines--chemistry
PubMed ID: 15845013
Date Deposited: 23 Jul 2013 15:55
Last Modified: 05 Feb 2019 16:55
URI: http://d-scholarship.pitt.edu/id/eprint/19394

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