Open AccessVisible-Light-Mediated C–H Alkylation of Pyridine Derivatives
Author(s) -
Fatima Rammal,
Di Gao,
Sondes Boujnah,
AnnieClaude Gaumont,
Aqeel A. Hussein,
Sami Lakhdar
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02863
Subject(s) - chemistry , alkylation , pyridine , quantum yield , reactivity (psychology) , yield (engineering) , density functional theory , selectivity , photochemistry , functional group , combinatorial chemistry , visible spectrum , reaction conditions , ion , computational chemistry , organic chemistry , catalysis , fluorescence , medicine , physics , alternative medicine , materials science , polymer , pathology , quantum mechanics , optoelectronics , metallurgy
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.
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