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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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Supplementary files

Article information


Submitted
19 Nov 2018
Accepted
03 Feb 2019
First published
08 Feb 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 3401-3407
Article type
Edge Article

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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