4.3 Article

Library-friendly synthesis of fluorinated ketones through functionalized hydration of alkynes and investigation of the reaction mechanism

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 132, Issue 10, Pages 804-810

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2011.05.006

Keywords

Cationic gold; Fluorination; Selectfluor; Fluoroketones; Alkynes

Funding

  1. National Science Foundation [CHE-0809683]
  2. CREAM Mass Spectrometry Facility (University of Louisville)
  3. NSF/EPSCoR [EPS-0447479]

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A library-friendly synthesis of alpha-substituted-alpha-fluoroketones through functionalized hydration of alkynes in one pot under mild conditions is reported. The ready availability of alkynes and organoboronic acids makes this reaction quite attractive. We also studied the key intermediate a fluorinated cationic gold species using in situ NMR spectroscopy and ESI-high resolution mass spectrometry. (C) 2011 Elsevier B.V. All rights reserved.

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