From Amines to Alkynes – Lighting the Way

14 June 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We present a metal-free photoredox strategy for the formation of Csp3-Csp bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridiniu salts with alkynyl tosylates, leading to functionalized alkynes , is easily scalable, offers broad substrate scope, high chemoselectivity, and mild conditions. Its potentials also highlighted by diversification of complex molecular scaffolds. Moreover, mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary, secondary and alkyl pyridinium salts.

Keywords

photoredox
metal-free
visible-light
catalysis
amine
alkyne
deaminative alkynylation
eosin Y
pyridinium salts

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