Visible-Light-Mediated C–H Alkylation of Pyridine Derivatives

We report herein a visible-light-mediated C–H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir­(ppy)3 under blue illumination. The mild reaction conditions together with the high gro...

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Bibliographic Details
Published in:Organic letters 2020-10, Vol.22 (19), p.7671-7675
Main Authors: Rammal, Fatima, Gao, Di, Boujnah, Sondes, Gaumont, Annie−Claude, Hussein, Aqeel A, Lakhdar, Sami
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary:We report herein a visible-light-mediated C–H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir­(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including density functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02863