Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification** Article Swipe
Yuxuan Ye
,
Seoung‐Tae Kim
,
Ryan P. King
,
Mu‐Hyun Baik
,
Stephen L. Buchwald
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202300109
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202300109
Pd‐catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. While investigating the Pd‐catalyzed fluorination of cyclic vinyl triflates, we observed that the addition of a substoichiometric quantity of TESCF 3 significantly improved the regioselectivity of the reaction. Herein, we report a combined experimental and computational study on the mechanism of this transformation focusing on the role of TESCF 3 . The poor regioselectivity of the reaction in the absence of additives results from the formation of LPd‐cyclohexyne complexes (L=biaryl monophosphine ligand). When TESCF 3 is added to the reaction mixture, the generation of the Pd‐cyclohexyne complexes is diminished by an unexpected pathway involving the dearomatization of the ligand by nucleophilic attack from a trifluoromethyl anion (CF 3 − ).
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/anie.202300109
- OA Status
- green
- Cited By
- 4
- References
- 62
- Related Works
- 10
- OpenAlex ID
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All OpenAlex metadata
Raw OpenAlex JSON
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https://openalex.org/W4320179461Canonical identifier for this work in OpenAlex
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https://doi.org/10.1002/anie.202300109Digital Object Identifier
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Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification**Work title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
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2023-02-12Full publication date if available
- Authors
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Yuxuan Ye, Seoung‐Tae Kim, Ryan P. King, Mu‐Hyun Baik, Stephen L. BuchwaldList of authors in order
- Landing page
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https://doi.org/10.1002/anie.202300109Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
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https://pmc.ncbi.nlm.nih.gov/articles/PMC10161128/pdf/nihms-1874559.pdfDirect OA link when available
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Regioselectivity, Chemistry, Nucleophile, Ligand (biochemistry), Trifluoromethyl, Structural isomer, Catalysis, Combinatorial chemistry, Reaction mechanism, Organic chemistry, Receptor, Alkyl, BiochemistryTop concepts (fields/topics) attached by OpenAlex
- Cited by
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4Total citation count in OpenAlex
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2024: 2, 2023: 2Per-year citation counts (last 5 years)
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10Other works algorithmically related by OpenAlex
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