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

Dhananjayan Vasu; Ángel L. Fuentes de Arriba; Jamie Leitch; Antoine de Gombert; Darren J. Dixon

doi:10.26434/chemrxiv.6653381.v4

Organic Chemistry

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

17 September 2018, Version 4

Working Paper

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This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

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.

Keywords

amine

C-H functionalization

Supplementary materials

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AminetoamineESI-14.09.2018

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crystallographic data

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