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Title: Synthesis of [ 18F]arenes via the copper-mediated [ 18F]fluorination of boronic acids

Here, a copper-mediated radiofluorination of aryl- and vinylboronic acids with K 18F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [ 18F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.
Authors:
 [1] ;  [1] ;  [2] ;  [2] ;  [2] ;  [2] ;  [3]
  1. Univ. of Michigan Medical School, Ann Arbor, MI (United States)
  2. Univ. of Michigan, Ann Arbor, MI (United States)
  3. Univ. of Michigan Medical School, Ann Arbor, MI (United States); Univ. of Michigan, Ann Arbor, MI (United States)
Publication Date:
Grant/Contract Number:
SC0012484
Type:
Published Article
Journal Name:
Organic Letters
Additional Journal Information:
Journal Volume: 17; Journal Issue: 23; Journal ID: ISSN 1523-7060
Publisher:
American Chemical Society
Research Org:
Univ. of Michigan, Ann Arbor, MI (United States)
Sponsoring Org:
USDOE Office of Science (SC)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1225990
Alternate Identifier(s):
OSTI ID: 1345033

Mossine, Andrew V., Brooks, Allen F., Makaravage, Katarina J., Miller, Jason M., Ichiishi, Naoko, Sanford, Melanie S., and Scott, Peter J. H.. Synthesis of [18F]arenes via the copper-mediated [18F]fluorination of boronic acids. United States: N. p., Web. doi:10.1021/acs.orglett.5b02875.
Mossine, Andrew V., Brooks, Allen F., Makaravage, Katarina J., Miller, Jason M., Ichiishi, Naoko, Sanford, Melanie S., & Scott, Peter J. H.. Synthesis of [18F]arenes via the copper-mediated [18F]fluorination of boronic acids. United States. doi:10.1021/acs.orglett.5b02875.
Mossine, Andrew V., Brooks, Allen F., Makaravage, Katarina J., Miller, Jason M., Ichiishi, Naoko, Sanford, Melanie S., and Scott, Peter J. H.. 2015. "Synthesis of [18F]arenes via the copper-mediated [18F]fluorination of boronic acids". United States. doi:10.1021/acs.orglett.5b02875.
@article{osti_1225990,
title = {Synthesis of [18F]arenes via the copper-mediated [18F]fluorination of boronic acids},
author = {Mossine, Andrew V. and Brooks, Allen F. and Makaravage, Katarina J. and Miller, Jason M. and Ichiishi, Naoko and Sanford, Melanie S. and Scott, Peter J. H.},
abstractNote = {Here, a copper-mediated radiofluorination of aryl- and vinylboronic acids with K18F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [18F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.},
doi = {10.1021/acs.orglett.5b02875},
journal = {Organic Letters},
number = 23,
volume = 17,
place = {United States},
year = {2015},
month = {11}
}