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Title: Preparation of o-fluorophenols from nonaromatic precursors: Mechanistic considerations for adaptation to fluorine-18 radiolabeling

Abstract

The preparation of fluorine-18 labeled o-fluorophenols at high specific activity is challenging and requires use of [ 18F]fluoride ion as the radioisotope source. As a novel, alternative approach, in this study we found that treatment of α-diazocyclohexenones with Selectfluor and Et 3N·3HF followed by HF elimination and tautomerization afforded o-fluorophenols regioselectively and rapidly. Finally, to adapt this chemistry to 18F radiolabeling, using bromine electrophiles in place of Selectfluor gave the o-fluorophenol via an α-bromo-α-fluoroketone intermediate in lower but still reasonable yields.

Authors:
 [1];  [1];  [1]
  1. Univ. of Illinois at Urbana-Champaign, Urbana, IL (United States)
Publication Date:
Research Org.:
Univ. of Illinois at Urbana-Champaign, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1345022
Grant/Contract Number:  
SC0005434; SC0008432
Resource Type:
Accepted Manuscript
Journal Name:
Organic Letters
Additional Journal Information:
Journal Volume: 17; Journal Issue: 22; Journal ID: ISSN 1523-7060
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Yasui, Norio, Mayne, Christopher G., and Katzenellenbogen, John A. Preparation of o-fluorophenols from nonaromatic precursors: Mechanistic considerations for adaptation to fluorine-18 radiolabeling. United States: N. p., 2015. Web. doi:10.1021/acs.orglett.5b02640.
Yasui, Norio, Mayne, Christopher G., & Katzenellenbogen, John A. Preparation of o-fluorophenols from nonaromatic precursors: Mechanistic considerations for adaptation to fluorine-18 radiolabeling. United States. doi:10.1021/acs.orglett.5b02640.
Yasui, Norio, Mayne, Christopher G., and Katzenellenbogen, John A. Wed . "Preparation of o-fluorophenols from nonaromatic precursors: Mechanistic considerations for adaptation to fluorine-18 radiolabeling". United States. doi:10.1021/acs.orglett.5b02640. https://www.osti.gov/servlets/purl/1345022.
@article{osti_1345022,
title = {Preparation of o-fluorophenols from nonaromatic precursors: Mechanistic considerations for adaptation to fluorine-18 radiolabeling},
author = {Yasui, Norio and Mayne, Christopher G. and Katzenellenbogen, John A.},
abstractNote = {The preparation of fluorine-18 labeled o-fluorophenols at high specific activity is challenging and requires use of [18F]fluoride ion as the radioisotope source. As a novel, alternative approach, in this study we found that treatment of α-diazocyclohexenones with Selectfluor and Et3N·3HF followed by HF elimination and tautomerization afforded o-fluorophenols regioselectively and rapidly. Finally, to adapt this chemistry to 18F radiolabeling, using bromine electrophiles in place of Selectfluor gave the o-fluorophenol via an α-bromo-α-fluoroketone intermediate in lower but still reasonable yields.},
doi = {10.1021/acs.orglett.5b02640},
journal = {Organic Letters},
number = 22,
volume = 17,
place = {United States},
year = {2015},
month = {11}
}

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Cited by: 6 works
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