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

preprint
revised on 17.09.2018 and posted on 17.09.2018 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.

History

Email Address of Submitting Author

darren.dixon@chem.ox.ac.uk

Institution

University of Oxford

Country

United Kingdom

ORCID For Submitting Author

0000-0003-2456-5236

Declaration of Conflict of Interest

No conflict of interest

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