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Issue 17, 2014
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Synthesis of α-tribromomethylamines via Mg-mediated addition of bromoform to imines

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Abstract

Mg-mediated addition of bromoform to electron deficient imines such as N-sulfonylimines affords α-tribromomethylated N-sulfonylamines in good to excellent yields. The procedure could be further simplified by transforming the imine precursors, α-sulfonyl-N-tosyl- and Boc-amines, in one pot to the corresponding α-tribromomethyl derivatives. Facile removal of the Boc protecting group in nearly quantitative yield and a silver carbonate mediated monodebromination have also been demonstrated.

Graphical abstract: Synthesis of α-tribromomethylamines via Mg-mediated addition of bromoform to imines

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Publication details

The article was received on 04 Feb 2014, accepted on 26 Feb 2014 and first published on 26 Feb 2014


Article type: Paper
DOI: 10.1039/C4OB00259H
Citation: Org. Biomol. Chem., 2014,12, 2769-2777
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    Synthesis of α-tribromomethylamines via Mg-mediated addition of bromoform to imines

    E. Gopi and I. N. N. Namboothiri, Org. Biomol. Chem., 2014, 12, 2769
    DOI: 10.1039/C4OB00259H

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