ArticleJournal of the American Chemical Society2018
Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Cobalt-catalyzed asymmetric three-component reductive addition of alkynes with alkyl halides and imines.Nature communications · 2026Article
- Catalytic 1,2-Migratory Insertion in a Bismuth Redox Platform: Reductive Arylation of Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Nickel-catalyzed electrophiles-controlled enantioselective reductive arylative cyclization and enantiospecific reductive alkylative cyclization of 1,6-enynes.Nature communications · 2024Article
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
- Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes to access stereodefined allylic alcohols.Chemical science · 2023Article
- Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.ACS catalysis · 2022Article
- Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis.Nature catalysis · 2021Article
- Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group.Nature communications · 2021Article
- Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates.ACS omega · 2018Article
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Authors and funding
2 authors.
Funding
Abstract
Nickel-catalyzed cross-electrophile couplings have recently emerged as highly effective and practical methods for the formation of C-C bonds. By merging this process with well-established π-π coupling chemistry, a new method for the synthesis of tetrasubstituted alkenes has been developed. The procedure relies on the use of chlorosilanes as a means of generating reactive vinylnickel intermediates, which are capable of undergoing a reductive cross-electrophile coupling with alkyl halides. The method not only generates highly substituted allylic alcohol derivatives but also obviates the need for stoichiometric organometallic nucleophiles and provides greatly improved scope and functional group tolerance compared with previously developed methods.
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