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Primary α-Tertiary Amine Synthesis via α-C–H Functionalization

revised on 17.09.2018, 11:13 and posted on 17.09.2018, 15:40 by Dhananjayan Vasu, Ángel L. Fuentes de Arriba, Jamie Leitch, Antoine de Gombert, Darren J. Dixon
A quinone-mediated general 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. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the late stage functionalization of drug molecules.


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University of Oxford


United Kingdom

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No conflict of interest