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Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis.

  • Jackl MK Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich , 8093 Zurich, Switzerland.
  • Legnani L Max-Planck-Institut für Kohlenforschung , 45470 Mülheim an der Ruhr, Germany.
  • Morandi B Max-Planck-Institut für Kohlenforschung , 45470 Mülheim an der Ruhr, Germany.
  • Bode JW Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich , 8093 Zurich, Switzerland.
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  • 2017-08-17
Published in:
  • Organic letters. - 2017
Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry
English Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.
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  • English
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green
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https://folia.unifr.ch/global/documents/104369
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