Issue 17, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Feb 2014
Accepted
26 Feb 2014
First published
26 Feb 2014

Org. Biomol. Chem., 2014,12, 2769-2777

Author version available

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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