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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: bodeorg.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 (free Supporting Information)


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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