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@ARTICLE{Ermert:863799,
      author       = {Ermert, Johannes and Meleán, Johnny Castillo and Humpert,
                      Swen and Modemann, Daniel and Krupp, Dominik and Kern,
                      Isabel and Kreft, Sabrina and Coenen, Heinrich Hubert},
      title        = {{B}aeyer-{V}illiger oxidation tuned to chemoselective
                      conversion of non-activated [18{F}]fluorobenzaldehydes to
                      [18{F}]fluorophenols},
      journal      = {Journal of labelled compounds and radiopharmaceuticals},
      volume       = {62},
      number       = {8},
      issn         = {0362-4803},
      address      = {New York, NY [u.a.]},
      publisher    = {Wiley},
      reportid     = {FZJ-2019-03786},
      pages        = {380 - 392},
      year         = {2019},
      abstract     = {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.},
      cin          = {INM-5},
      ddc          = {610},
      cid          = {I:(DE-Juel1)INM-5-20090406},
      pnm          = {573 - Neuroimaging (POF3-573)},
      pid          = {G:(DE-HGF)POF3-573},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:31026351},
      UT           = {WOS:000475397300004},
      doi          = {10.1002/jlcr.3740},
      url          = {https://juser.fz-juelich.de/record/863799},
}