Ruthenium-catalysed isomerisation–methylenation of allyl alcohols with methanol: a one-pot synthesis of substituted pyridines

A simple bench-stable ruthenium complex facilitates the synthesis of tetra-substituted pyridines in one pot <i>via</i> isomerisation-methylenation of allyl alcohol using methanol as a C1 source. This methodology is applicable to a broad range of electronically diverse diaryl and monoaryl allyl alcohols, making it highly robust for synthesising substituted pyridines. Mechanistic investigations, including control experiments and isotope labelling studies, demonstrate the involvement of metal hydride species in the isomerisation-methylenation of allyl alcohol. Additionally, many of the tetra-substituted pyridines synthesised using this methodology exhibited good photophysical properties, illustrating its potential to generate interesting materials with applicability in organic electronics.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00881f
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
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article

Ruthenium-catalysed isomerisation–methylenation of allyl alcohols with methanol: a one-pot synthesis of substituted pyridines

Vadapalli Chandrasekhar, Krishnan Venkatasubbaiah, Shaikh Samser, Basava Punna Rao Aradhyula et al.
Organic & Biomolecular Chemistry
Asymmetric Hydrogenation and Catalysis
article

Ruthenium-catalysed isomerisation–methylenation of allyl alcohols with methanol: a one-pot synthesis of substituted pyridines

Vadapalli Chandrasekhar, Krishnan Venkatasubbaiah, Shaikh Samser, Basava Punna Rao Aradhyula, Priyabrata Biswal, Sanu Siyad Pullarat
article en

Abstract

A simple bench-stable ruthenium complex facilitates the synthesis of tetra-substituted pyridines in one pot <i>via</i> isomerisation-methylenation of allyl alcohol using methanol as a C1 source. This methodology is applicable to a broad range of electronically diverse diaryl and monoaryl allyl alcohols, making it highly robust for synthesising substituted pyridines. Mechanistic investigations, including control experiments and isotope labelling studies, demonstrate the involvement of metal hydride species in the isomerisation-methylenation of allyl alcohol. Additionally, many of the tetra-substituted pyridines synthesised using this methodology exhibited good photophysical properties, illustrating its potential to generate interesting materials with applicability in organic electronics.

Organic & Biomolecular ChemistryVol. 23(29)
National Institute of Science Education and Research (IN), Homi Bhabha National Institute (IN), TIFR Centre for Interdisciplinary Sciences (IN)
Openalex Percentile: Top 88%
Asymmetric Hydrogenation and Catalysis
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Ruthenium-catalysed isomerisation–methylenation of allyl alcohols with methanol: a one-pot synthesis of substituted pyridines — Vadapalli Chandrasekhar, Krishnan Venkatasubbaiah, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS