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

Jackl, Moritz K.; Legnani, Luca; Morandi, Bill; Bode, Jeffrey W.

doi:10.1021/acs.orglett.7b02395

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

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Legnani, Luca
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi, Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Jackl, M. K., Legnani, L., Morandi, B., & Bode, J. W. (2017). Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis. Organic Letters, 19(17), 4696-4699. doi:10.1021/acs.orglett.7b02395.

Cite as: https://hdl.handle.net/21.11116/0000-0000-F752-D

Abstract

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.