Photochemical C–H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms

Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C–H silylation and hy...

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Bibliographic Details
Published in:ACS catalysis 2020-11, Vol.10 (22), p.13710-13717
Main Authors: Rammal, Fatima, Gao, Di, Boujnah, Sondes, Hussein, Aqeel A, Lalevée, Jacques, Gaumont, Annie-Claude, Morlet-Savary, Fabrice, Lakhdar, Sami
Format: Article
Language:English
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Chemical Sciences
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Summary:Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C–H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily available N-methoxypyridinium ions with a low catalyst loading (2 mol %) under blue light irradiation. The synthetic importance of the developed reactions is demonstrated by the synthesis of biologically relevant compounds. Electron paramagnetic resonance spectroscopy, quantum yield measurements, and density-functional theory calculations allowed us to understand reaction mechanisms of both photocatalytic reactions.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c03726