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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0000-F752-D Version Permalink: https://hdl.handle.net/21.11116/0000-0000-F753-C
Genre: Journal Article

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 Creators:
Jackl, Moritz K.1, Author
Legnani, Luca2, Author           
Morandi, Bill2, Author           
Bode, Jeffrey W.1, Author
Affiliations:
1Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland, ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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 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.

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Language(s): eng - English
 Dates: 2017-08-032017-08-162017-09-01
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.orglett.7b02395
 Degree: -

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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 19 (17) Sequence Number: - Start / End Page: 4696 - 4699 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338