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Fluorous synthesis with fewer fluorines (light fluorous synthesis): Separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel

Curran, DP and Luo, Z (1999) Fluorous synthesis with fewer fluorines (light fluorous synthesis): Separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel. Journal of the American Chemical Society, 121 (39). 9069 - 9072. ISSN 0002-7863

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Abstract

Fluorous synthesis involves tagging an organic substrate with a fluorinated tag for the purposes of separation. To date, techniques of fluorous synthesis have relied on liquid-liquid extractions. This paper applies a simple solid-liquid extraction procedure over fluorous reverse- phase silica gel (silica with a fluorocarbon bonded phase) for use in fluorous synthesis. Four amino acids were tagged on nitrogen with the C9F19COgroup, and the resulting acids were coupled in a parallel experiment with an excess of four amines. The resulting 16 crude fluorous amide products were separated from all the coupling reagents and excess amine by twostage filtration through fluorous silica. In 15 of the 16 cases, the products were isolated in good to excellent yield and purity. All of the products are soluble in organic solvents and none is expected to have any significant solubility in fluorous solvents, so the experiment dramatically illustrates the advantages of the solid-liquid extraction over the liquid- liquid extraction. Future prospects for application of fluorous silica are briefly discussed.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Luo, Z
Date: 6 October 1999
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 121
Number: 39
Page Range: 9069 - 9072
DOI or Unique Handle: 10.1021/ja991496r
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
Date Deposited: 26 Feb 2014 17:10
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20646

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