Selective Halogenation of Pyridines Using Designed Phosphine Reagents Article Swipe
Jeffrey N. Levy
,
Juan V. Alegre‐Requena
,
Renrong Liu
,
Robert S. Paton
,
Andrew McNally
·
YOU?
·
· 2020
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.0c04674
YOU?
·
· 2020
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.0c04674
Halopyridines are key building blocks for synthesizing pharmaceuticals, agrochemicals, and ligands for metal complexes, but strategies to selectively halogenate pyridine C-H precursors are lacking. We designed a set of heterocyclic phosphines that are installed at the 4-position of pyridines as phosphonium salts and then displaced with halide nucleophiles. A broad range of unactivated pyridines can be halogenated, and the method is viable for late-stage halogenation of complex pharmaceuticals. Computational studies indicate that C-halogen bond formation occurs via an SNAr pathway, and phosphine elimination is the rate-determining step. Steric interactions during C-P bond cleavage account for differences in reactivity between 2- and 3-substituted pyridines.
Related Topics
Concepts
Chemistry
Halogenation
Phosphine
Steric effects
Nucleophile
Pyridine
Reagent
Phosphonium
Reactivity (psychology)
Nucleophilic aromatic substitution
Halogen
Combinatorial chemistry
Electrophile
Bond cleavage
Halide
Organic chemistry
Medicinal chemistry
Nucleophilic substitution
Alkyl
Pathology
Catalysis
Medicine
Alternative medicine
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/jacs.0c04674
- OA Status
- green
- Cited By
- 80
- References
- 84
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3030507091
All OpenAlex metadata
Raw OpenAlex JSON
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https://openalex.org/W3030507091Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/jacs.0c04674Digital Object Identifier
- Title
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Selective Halogenation of Pyridines Using Designed Phosphine ReagentsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2020Year of publication
- Publication date
-
2020-05-29Full publication date if available
- Authors
-
Jeffrey N. Levy, Juan V. Alegre‐Requena, Renrong Liu, Robert S. Paton, Andrew McNallyList of authors in order
- Landing page
-
https://doi.org/10.1021/jacs.0c04674Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
-
https://www.ncbi.nlm.nih.gov/pmc/articles/7526642Direct OA link when available
- Concepts
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Chemistry, Halogenation, Phosphine, Steric effects, Nucleophile, Pyridine, Reagent, Phosphonium, Reactivity (psychology), Nucleophilic aromatic substitution, Halogen, Combinatorial chemistry, Electrophile, Bond cleavage, Halide, Organic chemistry, Medicinal chemistry, Nucleophilic substitution, Alkyl, Pathology, Catalysis, Medicine, Alternative medicineTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
80Total citation count in OpenAlex
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2025: 20, 2024: 17, 2023: 10, 2022: 14, 2021: 13Per-year citation counts (last 5 years)
- References (count)
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84Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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