Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
Moritz K. Jackl, Luca Legnani, Bill Morandi and Jeffrey W. Bode*
*Laboratory of Organic Chemistry, Department of Chemistry and
Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland, Email: bode
org.chem.ethz.ch
M. K. Jackl, L. Legnani, B. Morandi, J. W. Bode, Org. Lett., 2017, 19, 4696-4699.
DOI: 10.1021/acs.orglett.7b02395
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Abstract
A scalable, photocatalytic coupling of silicon amine protocol (SLAP) reagents and aldehydes provides substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions in the presence of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive.
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proposed mechanism
Key Words
morpholines, thiomorpholines, photochemistry, flow chemistry
ID: J54-Y2017
