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Issue 11, 2019
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Primary α-tertiary amine synthesis via α-C–H functionalization

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Abstract

A quinone-mediated general synthetic platform for the construction of primary α-tertiary amines from abundant primary α-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles, via a nucleophilic α-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.

Graphical abstract: Primary α-tertiary amine synthesis via α-C–H functionalization

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Publication details

The article was received on 19 Nov 2018, accepted on 03 Feb 2019 and first published on 08 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05164J
Citation: Chem. Sci., 2019,10, 3401-3407
  • Open access: Creative Commons BY license
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    Primary α-tertiary amine synthesis via α-C–H functionalization

    D. Vasu, A. L. Fuentes de Arriba, J. A. Leitch, A. de Gombert and D. J. Dixon, Chem. Sci., 2019, 10, 3401
    DOI: 10.1039/C8SC05164J

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