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Direct Synthesis of Unprotected 2-Azidoamines from Alkenes via an Iron-Catalyzed Difunctionalization Reaction

Szabolcs Makai, Eric Falk and Bill Morandi*

*ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, Email:

S. Makai, E. Falk, B. Morandi, J. Am. Chem. Soc., 2020, 142, 21548-21555.

DOI: 10.1021/jacs.0c11025 (free Supporting Information)

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An operationally simple iron-catalyzed difunctionalization of alkenes provides primary 2-azidoamines, which are versatile precursors to vicinal diamines. A wide array of alkene substrates are tolerated, including complex drug-like molecules and a tripeptide. Facile, chemoselective derivatizations of the azidoamine group demonstrate the versatility of this masked diamine motif.

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Key Words

benzylic azides, alkyl azides, diamination

ID: J48-Y2020