Home > Publications database > Baeyer-Villiger oxidation tuned to chemoselective conversion of non-activated [18F]fluorobenzaldehydes to [18F]fluorophenols > print

001     863799
005     20210130002323.0
024 7 _ |a 10.1002/jlcr.3740
|2 doi
024 7 _ |a 0022-2135
|2 ISSN
024 7 _ |a 0362-4803
|2 ISSN
024 7 _ |a 1099-1344
|2 ISSN
024 7 _ |a 1559-0860
|2 ISSN
024 7 _ |a pmid:31026351
|2 pmid
024 7 _ |a WOS:000475397300004
|2 WOS
037 _ _ |a FZJ-2019-03786
082 _ _ |a 610
100 1 _ |a Ermert, Johannes
|0 P:(DE-Juel1)131818
|b 0
|e Corresponding author
245 _ _ |a Baeyer-Villiger oxidation tuned to chemoselective conversion of non-activated [18F]fluorobenzaldehydes to [18F]fluorophenols
260 _ _ |a New York, NY [u.a.]
|c 2019
|b Wiley
336 7 _ |a article
|2 DRIVER
336 7 _ |a Output Types/Journal article
|2 DataCite
336 7 _ |a Journal Article
|b journal
|m journal
|0 PUB:(DE-HGF)16
|s 1563276175_389
|2 PUB:(DE-HGF)
336 7 _ |a ARTICLE
|2 BibTeX
336 7 _ |a JOURNAL_ARTICLE
|2 ORCID
336 7 _ |a Journal Article
|0 0
|2 EndNote
520 _ _ |a A reaction pathway via oxidation of [18F]fluorobenzaldehydes offers a very useful tool for the no‐carrier‐added radiosynthesis of [18F]fluorophenols, a structural motive of several potential radiopharmaceuticals. A considerably improved chemoselectivity of the Baeyer‐Villiger oxidation (BVO) towards phenols was achieved, employing 2,2,2‐trifluoroethanol as reaction solvent in combination with Oxone or m‐CPBA as oxidation agent. The studies showed the necessity of H2SO4 addition, which appears to have a dual effect, acting as catalyst and desiccant. For example, 2‐[18F]fluorophenol was obtained with a RCY of 97% under optimised conditions of 80°C and 30‐minute reaction time. The changed performance of the BVO, which is in agreement with known reaction mechanisms via Criegee intermediates, provided the best results with regard to radiochemical yield (RCY) and chemoselectivity, i.e. formation of [18F]fluorophenols rather than [18F]fluorobenzoic acids. Thus, after a long history of the BVO, the new modification now allows an almost specific formation of phenols, even from electron‐deficient benzaldehydes. Further, the applicability of the tuned, chemoselective BVO to the n.c.a. level and to more complex compounds was demonstrated for the products n.c.a. 4‐[18F]fluorophenol (RCY 95%; relating to 4‐[18F]fluorobenzaldehyde) and 4‐[18F]fluoro‐m‐tyramine (RCY 32%; relating to [18F]fluoride), respectively.
536 _ _ |a 573 - Neuroimaging (POF3-573)
|0 G:(DE-HGF)POF3-573
|c POF3-573
|f POF III
|x 0
588 _ _ |a Dataset connected to CrossRef
700 1 _ |a Meleán, Johnny Castillo
|0 P:(DE-HGF)0
|b 1
700 1 _ |a Humpert, Swen
|0 P:(DE-Juel1)132740
|b 2
|u fzj
700 1 _ |a Modemann, Daniel
|0 P:(DE-Juel1)162416
|b 3
|u fzj
700 1 _ |a Krupp, Dominik
|0 P:(DE-Juel1)168273
|b 4
700 1 _ |a Kern, Isabel
|0 P:(DE-HGF)0
|b 5
700 1 _ |a Kreft, Sabrina
|0 P:(DE-Juel1)144437
|b 6
700 1 _ |a Coenen, Heinrich Hubert
|0 P:(DE-Juel1)131816
|b 7
|u fzj
773 _ _ |a 10.1002/jlcr.3740
|g Vol. 62, no. 8, p. 380 - 392
|0 PERI:(DE-600)1491841-9
|n 8
|p 380 - 392
|t Journal of labelled compounds and radiopharmaceuticals
|v 62
|y 2019
|x 0362-4803
856 4 _ |u https://juser.fz-juelich.de/record/863799/files/BVO%20on%20non-activated%20benzaldehydes%202019.04.12.pdf
|y Restricted
856 4 _ |u https://juser.fz-juelich.de/record/863799/files/BVO%20on%20non-activated%20benzaldehydes%202019.04.12.pdf?subformat=pdfa
|x pdfa
|y Restricted
856 4 _ |u https://juser.fz-juelich.de/record/863799/files/Ermert_et_al-2019-Journal_of_Labelled_Compounds_and_Radiopharmaceuticals.pdf
|y Restricted
856 4 _ |u https://juser.fz-juelich.de/record/863799/files/Ermert_et_al-2019-Journal_of_Labelled_Compounds_and_Radiopharmaceuticals.pdf?subformat=pdfa
|x pdfa
|y Restricted
909 C O |o oai:juser.fz-juelich.de:863799
|p VDB
910 1 _ |a Forschungszentrum Jülich
|0 I:(DE-588b)5008462-8
|k FZJ
|b 0
|6 P:(DE-Juel1)131818
910 1 _ |a Forschungszentrum Jülich
|0 I:(DE-588b)5008462-8
|k FZJ
|b 1
|6 P:(DE-HGF)0
910 1 _ |a Forschungszentrum Jülich
|0 I:(DE-588b)5008462-8
|k FZJ
|b 2
|6 P:(DE-Juel1)132740
910 1 _ |a Forschungszentrum Jülich
|0 I:(DE-588b)5008462-8
|k FZJ
|b 3
|6 P:(DE-Juel1)162416
910 1 _ |a Forschungszentrum Jülich
|0 I:(DE-588b)5008462-8
|k FZJ
|b 7
|6 P:(DE-Juel1)131816
913 1 _ |a DE-HGF
|b Key Technologies
|l Decoding the Human Brain
|1 G:(DE-HGF)POF3-570
|0 G:(DE-HGF)POF3-573
|2 G:(DE-HGF)POF3-500
|v Neuroimaging
|x 0
|4 G:(DE-HGF)POF
|3 G:(DE-HGF)POF3
914 1 _ |y 2019
915 _ _ |a Nationallizenz
|0 StatID:(DE-HGF)0420
|2 StatID
915 _ _ |a JCR
|0 StatID:(DE-HGF)0100
|2 StatID
|b J LABELLED COMPD RAD : 2017
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)0200
|2 StatID
|b SCOPUS
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)0300
|2 StatID
|b Medline
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)0600
|2 StatID
|b Ebsco Academic Search
915 _ _ |a Peer Review
|0 StatID:(DE-HGF)0030
|2 StatID
|b ASC
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)0199
|2 StatID
|b Clarivate Analytics Master Journal List
915 _ _ |a WoS
|0 StatID:(DE-HGF)0110
|2 StatID
|b Science Citation Index
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)0150
|2 StatID
|b Web of Science Core Collection
915 _ _ |a WoS
|0 StatID:(DE-HGF)0111
|2 StatID
|b Science Citation Index Expanded
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)1030
|2 StatID
|b Current Contents - Life Sciences
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)1150
|2 StatID
|b Current Contents - Physical, Chemical and Earth Sciences
915 _ _ |a DBCoverage
|0 StatID:(DE-HGF)1050
|2 StatID
|b BIOSIS Previews
915 _ _ |a IF < 5
|0 StatID:(DE-HGF)9900
|2 StatID
920 _ _ |l yes
920 1 _ |0 I:(DE-Juel1)INM-5-20090406
|k INM-5
|l Nuklearchemie
|x 0
980 _ _ |a journal
980 _ _ |a VDB
980 _ _ |a I:(DE-Juel1)INM-5-20090406
980 _ _ |a UNRESTRICTED

LibraryCollectionCLSMajorCLSMinorLanguageAuthor
Marc 21