ArticleNature communications2018
Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides.
Article in Nature communications, 2018. 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.
- Photoactivatable Electrophilic Glycosylselenosulfonates for Ultrafast Modification of Alkynes and Thiols.ACS central science · 2025Article
- Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se.Scientific reports · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides.Nature communications · 2024Article
- Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- C(spRSC advances · 2024Article
- Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.Chemical science · 2022Article
- Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy.Nature communications · 2022Article
- Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.Journal of the American Chemical Society · 2021Article
- Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C-S/C-N Couplings.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Microbiological versus Chemical Reductive Sulfidation: An Experimental and Theoretical Study.ACS omega · 2021Article
- Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C-S Formation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides.Chemical science · 2020Article
- Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates.Organic letters · 2020Article
- Article
- Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines.Nature communications · 2020Article
- Recent synthesis of thietanes.Beilstein journal of organic chemistry · 2020Review
- Nano-architecture of silica nanoparticles as a tool to tune both electrochemical and catalytic behavior of NiRSC advances · 2019Article
- Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols.Nature communications · 2019Article
- Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or HChemical science · 2019Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chalcogen-containing compounds have received considerable attention because of their manifold applications in agrochemicals, pharmaceuticals, and material science. While many classical methods have been developed for preparing organic sulfides, most of them exploited the transition-metal-catalyzed cross-couplings of aryl halides or pseudo halides with thiols or disulfides, with harsh reaction conditions usually being required. Herein, we present a user-friendly, nickel-catalyzed reductive thiolation of unactivated primary and secondary alkyl bromides with thiosulfonates as reliable thiolation reagents, which are easily prepared and bench-stable. Furthermore, a series of selenides is also prepared in a similar fashion with selenosulfonates as selenolation reagents. This catalytic method offers a facile synthesis of a wide range of unsymmetrical alkyl-aryl or alkyl-alkyl sulfides and selenides under mild conditions with an excellent tolerance of functional groups. Likewise, the use of sensitive and stoichiometric organometallic reagents can be avoided.
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