ArticleJournal of the American Chemical Society2014
Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Nickel-Catalyzed Enantioconvergent Arylation of Unactivated Cyclic Electrophiles: Asymmetric Synthesis of 3-Substituted Pyrrolidines.Angewandte Chemie (International ed. in English) · 2026Article
- Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides.Nature communications · 2024Article
- A general copper-catalysed enantioconvergent C(spNature chemistry · 2024Article
- Metal-Catalyzed Enantioconvergent Transformations.Chemical reviews · 2023Review
- Article
- Access to dialkylated allylic stereogenic centers by Ni-catalysed enantioselective hydrovinylation of unactivated alkenes.Chemical science · 2022Article
- Access to chiral β-sulfonyl carbonyl compoundsChemical science · 2022Article
- Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.Organic letters · 2022Article
- Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.Chemical science · 2022Article
- DFT insight into asymmetric alkyl-alkyl bond formationChemical science · 2022Article
- Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.Chemical reviews · 2021Article
- Nickel-catalyzed asymmetric reductive arylation of α-chlorosulfones with aryl halides.Chemical science · 2021Article
- Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.Angewandte Chemie (International ed. in English) · 2019Article
- Alkenylation of C(spAngewandte Chemie (International ed. in English) · 2018Article
- Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SACS central science · 2017Review
- Decarboxylative alkenylation.Nature · 2017Article
- Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.Journal of the American Chemical Society · 2017Article
- Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.Chemical reviews · 2017Article
- Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.Advanced synthesis & catalysis · 2016Article
- Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.Journal of the American Chemical Society · 2016Article
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3 authors.
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Abstract
The development of efficient methods for the generation of enantioenriched sulfonamides and sulfones is an important objective for fields such as organic synthesis and medicinal chemistry; however, there have been relatively few reports of direct catalytic asymmetric approaches to controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-catalyzed stereoconvergent Negishi arylations and alkenylations of racemic α-bromosulfonamides and -sulfones that furnish the desired cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate that has a sufficient lifetime to diffuse out of the solvent cage and to cyclize onto a pendant olefin.
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