A Mild and Catalyst‐Free Synthesis of Cannabidiols and Regioisomers Mediated by Fluorinated Alcohols Article Swipe
Phanomsak Yukhet
,
Kriangsak Faikhruea
,
Rewadee Mowang
,
Phiphob Naweephattana
,
Manussada Ratanasak
,
Yasuteru Shigeta
,
Thanyada Rungrotmongkol
,
Chanat Aonbangkhen
,
Tirayut Vilaivan
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/asia.202401648
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/asia.202401648
This study presents a novel and practical strategy for synthesizing cannabinoids using a fluorinated alcohol solvent for the first time. Hexafluoroisopropanol (HFIP) was found to efficiently promote intermolecular Friedel–Crafts alkylation between allylic alcohols and electron‐rich aromatics. This approach enabled the successful synthesis of cannabidiol (CBD) derivatives bearing various alkyl substituents, as well as the corresponding unnatural regioisomer (abnCBD), achieving moderate to high yields under mild conditions without the need for additional catalysts or other reagents. Insights in the mechanistic details were obtained through DFT calculations. Furthermore, a streamlined three‐step synthesis of 5‐alkyl resorcinol derivatives, essential starting materials for CBD synthesis, from the readily available chalcones was developed. Preliminary cytotoxicity assays using MTT revealed that some synthetic CBD derivatives exhibited promising anticancer activities.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/asia.202401648
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/asia.202401648
- OA Status
- bronze
- References
- 87
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4408243895
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4408243895Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1002/asia.202401648Digital Object Identifier
- Title
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A Mild and Catalyst‐Free Synthesis of Cannabidiols and Regioisomers Mediated by Fluorinated AlcoholsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2025Year of publication
- Publication date
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2025-03-11Full publication date if available
- Authors
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Phanomsak Yukhet, Kriangsak Faikhruea, Rewadee Mowang, Phiphob Naweephattana, Manussada Ratanasak, Yasuteru Shigeta, Thanyada Rungrotmongkol, Chanat Aonbangkhen, Tirayut VilaivanList of authors in order
- Landing page
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https://doi.org/10.1002/asia.202401648Publisher landing page
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/asia.202401648Direct link to full text PDF
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YesWhether a free full text is available
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bronzeOpen access status per OpenAlex
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/asia.202401648Direct OA link when available
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Structural isomer, Chemistry, Catalysis, Reagent, Alkylation, Combinatorial chemistry, Alkyl, Alcohol, Solvent, Intermolecular force, Organic chemistry, MoleculeTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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87Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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