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Title: Copper-Mediated Radiofluorination of Arylstannanes with [ 18F]KF

In this article, a copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [ 18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [ 18F]F-phenylalanine and [ 18F]F-DOPA. In addition, an automated synthesis of [ 18F]MPPF is demonstrated that delivers a clinically validated dose of 200 ± 20 mCi with a high specific activity of 2400 ± 900 Ci/mmol.
Authors:
 [1] ;  [2] ;  [2] ;  [1] ;  [3]
  1. Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemistry
  2. Univ. of Michigan Medical School, Ann Arbor, MI (United States). Dept. of Radiology
  3. Univ. of Michigan Medical School, Ann Arbor, MI (United States). Dept. of Radiology and the Interdepartmental Program in Medicinal Chemistry
Publication Date:
Grant/Contract Number:
SC0012484; R01EB021155
Type:
Published Article
Journal Name:
Organic Letters
Additional Journal Information:
Journal Volume: 18; Journal Issue: 20; Journal ID: ISSN 1523-7060
Publisher:
American Chemical Society
Research Org:
Univ. of Michigan Medical School, Ann Arbor, MI (United States)
Sponsoring Org:
USDOE; National Institutes of Health (NIH); Merck and Company, Inc., Kenilworth, NJ (United States)
Country of Publication:
United States
Language:
English
Subject:
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
OSTI Identifier:
1328258
Alternate Identifier(s):
OSTI ID: 1425388

Makaravage, Katarina J., Brooks, Allen F., Mossine, Andrew V., Sanford, Melanie S., and Scott, Peter J. H.. Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF. United States: N. p., Web. doi:10.1021/acs.orglett.6b02911.
Makaravage, Katarina J., Brooks, Allen F., Mossine, Andrew V., Sanford, Melanie S., & Scott, Peter J. H.. Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF. United States. doi:10.1021/acs.orglett.6b02911.
Makaravage, Katarina J., Brooks, Allen F., Mossine, Andrew V., Sanford, Melanie S., and Scott, Peter J. H.. 2016. "Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF". United States. doi:10.1021/acs.orglett.6b02911.
@article{osti_1328258,
title = {Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF},
author = {Makaravage, Katarina J. and Brooks, Allen F. and Mossine, Andrew V. and Sanford, Melanie S. and Scott, Peter J. H.},
abstractNote = {In this article, a copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [18F]F-phenylalanine and [18F]F-DOPA. In addition, an automated synthesis of [18F]MPPF is demonstrated that delivers a clinically validated dose of 200 ± 20 mCi with a high specific activity of 2400 ± 900 Ci/mmol.},
doi = {10.1021/acs.orglett.6b02911},
journal = {Organic Letters},
number = 20,
volume = 18,
place = {United States},
year = {2016},
month = {10}
}