ArticleJournal of the American Chemical Society2015
Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 155 citations in OpenAlex.
- Facile (Z)-Selective Synthesis of β,γ-Unsaturated Ketones by a Silicon-based Olefination Strategy.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Highly Substituted Alkenes from Terminal Alkynes.Journal of the American Chemical Society · 2025Article
- Iron-catalyzed alkyne alkylzincation affected by counterions.Nature communications · 2025Article
- Selective Synthesis ofJournal of the American Chemical Society · 2025Article
- Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping.Nature communications · 2024Article
- Regio- and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes.Nature communications · 2024Article
- Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024Article
- Iron-Catalyzed Reductive Cross-Coupling of Alkyl Electrophiles with Olefins.Angewandte Chemie (International ed. in English) · 2023Article
- Stereoselective Synthesis of Trisubstituted Alkenes via Copper Hydride-Catalyzed Alkyne Hydroalkylation.Journal of the American Chemical Society · 2023Article
- Cobalt-catalyzed branched selective hydroallylation of terminal alkynes.Nature communications · 2022Article
- Crossed Regio- and Enantioselective Iron-Catalyzed [4+2]-Cycloadditions of Unactivated Dienes.Angewandte Chemie (International ed. in English) · 2022Article
- Mechanism ofJournal of the American Chemical Society · 2021Article
- Hydroalkylation of Alkynes: Functionalization of the Alkenyl Copper Intermediate through Single Electron Transfer Chemistry.Journal of the American Chemical Society · 2021Article
- Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.Journal of the American Chemical Society · 2020Article
- Visible Light-Enabled spChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism.Angewandte Chemie (International ed. in English) · 2020Article
- Article
- Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons.Beilstein journal of organic chemistry · 2020Article
- A Carbene-Extended ATRA Reaction.Angewandte Chemie (International ed. in English) · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes. The method employs inexpensive and nontoxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups. The utility of the method is demonstrated in the synthesis of several pharmaceutically relevant molecules. Mechanistic study suggests that the reaction proceeds through an iron-catalyzed anti-selective carbozincation pathway.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.