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000863799 1001_ $$0P:(DE-Juel1)131818$$aErmert, Johannes$$b0$$eCorresponding author
000863799 245__ $$aBaeyer-Villiger oxidation tuned to chemoselective conversion of non-activated [18F]fluorobenzaldehydes to [18F]fluorophenols
000863799 260__ $$aNew York, NY [u.a.]$$bWiley$$c2019
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000863799 520__ $$aA reaction pathway via oxidation of [18F]fluorobenzaldehydes offers a very useful tool for the no‐carrier‐added radiosynthesis of [18F]fluorophenols, a structural motive of several potential radiopharmaceuticals. A considerably improved chemoselectivity of the Baeyer‐Villiger oxidation (BVO) towards phenols was achieved, employing 2,2,2‐trifluoroethanol as reaction solvent in combination with Oxone or m‐CPBA as oxidation agent. The studies showed the necessity of H2SO4 addition, which appears to have a dual effect, acting as catalyst and desiccant. For example, 2‐[18F]fluorophenol was obtained with a RCY of 97% under optimised conditions of 80°C and 30‐minute reaction time. The changed performance of the BVO, which is in agreement with known reaction mechanisms via Criegee intermediates, provided the best results with regard to radiochemical yield (RCY) and chemoselectivity, i.e. formation of [18F]fluorophenols rather than [18F]fluorobenzoic acids. Thus, after a long history of the BVO, the new modification now allows an almost specific formation of phenols, even from electron‐deficient benzaldehydes. Further, the applicability of the tuned, chemoselective BVO to the n.c.a. level and to more complex compounds was demonstrated for the products n.c.a. 4‐[18F]fluorophenol (RCY 95%; relating to 4‐[18F]fluorobenzaldehyde) and 4‐[18F]fluoro‐m‐tyramine (RCY 32%; relating to [18F]fluoride), respectively.
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000863799 7001_ $$0P:(DE-HGF)0$$aMeleán, Johnny Castillo$$b1
000863799 7001_ $$0P:(DE-Juel1)132740$$aHumpert, Swen$$b2$$ufzj
000863799 7001_ $$0P:(DE-Juel1)162416$$aModemann, Daniel$$b3$$ufzj
000863799 7001_ $$0P:(DE-Juel1)168273$$aKrupp, Dominik$$b4
000863799 7001_ $$0P:(DE-HGF)0$$aKern, Isabel$$b5
000863799 7001_ $$0P:(DE-Juel1)144437$$aKreft, Sabrina$$b6
000863799 7001_ $$0P:(DE-Juel1)131816$$aCoenen, Heinrich Hubert$$b7$$ufzj
000863799 773__ $$0PERI:(DE-600)1491841-9$$a10.1002/jlcr.3740$$gVol. 62, no. 8, p. 380 - 392$$n8$$p380 - 392$$tJournal of labelled compounds and radiopharmaceuticals$$v62$$x0362-4803$$y2019
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