Halogen-Bond-Induced Consecutive Csp³-H Aminations via Hydrogen Atom Transfer Relay Strategy

Fan Wu, Jeewani P. Ariyarathna, Navdeep Kaur, Nur-E Alom, Maureen L. Kennell, Omar H. Bassiouni and Wei Li*

*Department of Chemistry and Biochemistry, The University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States, Email: Wei.Liutoledo.edu

F. Wu, J. P. Ariyarathna, N. Kaur, N.-E. Alom, M. L. Kennell, O. H. Bassiouni, W. Li, Org. Lett., 2020, 22, 2135-2140.

DOI: 10.1021/acs.orglett.0c00081

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Abstract

Halogen bonding induces an intermolecular Csp³-H amination and even enables a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions.

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Key Words

sulfonamides, benzylic amines, NIS

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ID: J54-Y2020