ArticleACS catalysis2024
Sulfone Electrophiles in Cross-Electrophile Coupling: Nickel-Catalyzed Difluoromethylation of Aryl Bromides.
Article in ACS catalysis, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Photochemical Fluoroalkylations with Fluorinated Gases Facilitated by a Robust Metal-Organic Framework.Journal of the American Chemical Society · 2026Article
- Construction of CFBeilstein journal of organic chemistry · 2026Review
- Dual transition metal electrocatalysis for difluoromethylation of Aryl halides using potassium difluoroacetate.Nature communications · 2025Article
- A practical photocatalytic strategy for radical (deuterio)difluoromethylation using imidazolium reagents.Chemical science · 2025Article
- Defluorinative Coupling of (NH)-Heteroarenes and Unactivated Vinyl Fluorides Enabled by Metal-Organic Frameworks.Journal of the American Chemical Society · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Highly Enantioselective Decarboxylative Difluoromethylation.Journal of the American Chemical Society · 2024Article
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Authors and funding
6 authors.
Funding
Abstract
Fluoroalkyl fragments have played a critical role in the design of pharmaceutical and agrochemical molecules in recent years due to the enhanced biological properties of fluorinated molecules compared to their non-fluorinated analogues. Despite the potential advantages conferred by incorporating a difluoromethyl group in organic compounds, industrial adoption of difluoromethylation methods lags behind fluorination and trifluoromethylation. This is due in part to challenges in applying common difluoromethyl sources towards industrial applications. We report here the nickel-catalyzed cross-electrophile coupling of (hetero)aryl bromides with difluoromethyl 2-pyridyl sulfone, a sustainably sourced, crystalline difluoromethylation reagent. The scope of this reaction is demonstrated with 24 examples (67 ± 16% average yield) including a diverse array of heteroaryl bromides and precursors to difluoromethyl-containing preclinical pharmaceuticals. This reaction can be applied to small-scale parallel synthesis and benchtop scale-up under mild conditions. As sulfone reagents are uncommon electrophiles in cross-electrophile coupling, the mechanism of this process was investigated. Studies confirmed the formation of •CF
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