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Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

Carlos R. Gonçalves, Miran Lemmerer, Christopher J. Teskey, Pauline Adler, Daniel Kaiser, Boris Maryasin, Leticia González and Nuno Maulide*

*Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria, Email: nuno.maulideunivie.ac.at

C. R. Gonçalves, M. Lemmerer, C. J. Teskey, P. Adler, D. Kaiser, B. Maryasin, L. González, N. Maulide, J. Am. Chem. Soc., 2019, 141, 18437-18443.

DOI: 10.1021/jacs.9b06956 (free Supporting Information)


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Abstract

By rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides.

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Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

A. de la Torre, D. Kaiser, N. Maulide, J. Am. Chem. Soc., 2017, 139, 6578-6581.

Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides

V. Tona, A. de la Torre, M. Padmanaban, S. Ruider, L. González, N. Maulide, J. Am. Chem. Soc., 2016, 138, 8348-8351.


Key Words

α-chlorination, α-bromination, α-iodination, α-hydroxylation, α-amination, sulfonamides, sulfides, pyridine N-oxides


ID: J48-Y2019