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Synthesis of Halogenated Anilines by Treatment of N,N-Dialkylaniline N-Oxides with Thionyl Halides

Year: 2018
Type: article
Abstract: The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N- O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
DOI: 10.1021/acs.joc.8b01590
Authors: Hayley Reed, Tyler R. Paul, William J. Chain
Language: English
Field: Chemistry
Open Access status: green
Funders: University of Delaware, National Institutes of Health, American Chemical Society Petroleum Research Fund, NIH Office of the Director, National Institute of General Medical Sciences, National Center for Research Resources, Division of Chemistry
Awards: G1617517245, G2144188405, Discovery of Chemical Probes and Therapeutic Leads, Phase II, G335888736, G4040836280, G501384772, G5679962385, G6204561026, High Performance Digital NMR Spectrometer, Molecular Design of Advanced Biomaterials, Q-Exactive Orbitrap LC-MC/MS System
OpenAlex ID: W2884097537
FWCI: 0.409
Cites: 38
Cited by: 13
Related to: 10