ArticleNature communications2019
Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Metal-Hydride C-C Cross-Coupling of Alkenes Through a Double Outer-Sphere Mechanism.The Journal of organic chemistry · 2024Review
- Ni-catalysed remote C(spNature reviews. Chemistry · 2024Review
- Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides.Nature communications · 2024Article
- Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes.Nature communications · 2024Article
- Ligand Relay Catalysis Enables Asymmetric Migratory Hydroarylation for the Concise Synthesis of Chiral α-(Hetero)Aryl-Substituted Amines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- RegiodivergentJACS Au · 2023Review
- Elucidating electron-transfer events in polypyridine nickel complexes for reductive coupling reactions.Nature catalysis · 2023Article
- NiH-catalyzed anti-Markovnikov hydroamidation of unactivated alkenes with 1,4,2-dioxazol-5-ones for the direct synthesis of N-alkyl amides.Communications chemistry · 2022Article
- Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates.Nature communications · 2022Article
- Regio- and enantioselective remote hydroarylation using a ligand-relay strategy.Nature communications · 2022Article
- γ-Selective C(spNature communications · 2021Article
- Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes.Journal of the American Chemical Society · 2021Article
- Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes.Nature communications · 2021Article
- NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines.Nature communications · 2021Article
- Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates.Organic letters · 2020Article
- Decarboxylative thiolation of redox-active esters to free thiols and further diversification.Nature communications · 2020Article
- Migratory functionalization of unactivated alkyl bromides for construction of all-carbon quaternary centers via transposed tert-C-radicals.Nature communications · 2020Article
- Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequentChemical science · 2020Article
- Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process.Molecules (Basel, Switzerland) · 2020Article
- Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes.Journal of the American Chemical Society · 2019Article
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Authors and funding
3 authors.
Funding
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Abstract
Direct (utilize easily available and abundant precursors) and selective (both chemo- and regio-) aliphatic C-H functionalization is an attractive mean with which to streamline chemical synthesis. With many possible sites of reaction, traditional methods often need an adjacent polar directing group nearby to achieve high regio- and chemoselectivity and are often restricted to a single site of functionalization. Here we report a remote aliphatic C-H thiolation process with predictable and switchable regioselectivity through NiH-catalysed migratory hydrothiolation of two feedstock chemicals (alkenes/alkynes and thiols). This mild reaction avoids the preparation of electrophilic thiolation reagents and is highly selective to thiols over other nucleophilic groups, such as alcohols, acids, amines, and amides. Mechanistic studies show that the reaction occurs through the formation of an RS-Bpin intermediate, and THF as the solvent plays an important role in the regeneration of NiH species.
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