ArticleJournal of the American Chemical Society2014
Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition.
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.
- Facile (Z)-Selective Synthesis of β,γ-Unsaturated Ketones by a Silicon-based Olefination Strategy.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes.Journal of the American Chemical Society · 2024Article
- Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne.Journal of the American Chemical Society · 2022Article
- Dual utility of a single diphosphine-ruthenium complex: a precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation.RSC advances · 2021Article
- Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in CarbonylJournal of the American Chemical Society · 2021Article
- Enantioselective Addition of α-Nitroesters to Alkynes.Angewandte Chemie (International ed. in English) · 2021Article
- Synthesis of Isomerically Pure (Journal of the American Chemical Society · 2019Article
- A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes.Chemical science · 2019Article
- Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.Journal of the American Chemical Society · 2019Article
- Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.Chemical reviews · 2018Review
- Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.Chemical science · 2018Article
- A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.Journal of the American Chemical Society · 2018Article
- Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.Accounts of chemical research · 2017Article
- Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.Organic letters · 2017Article
- Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.Angewandte Chemie (International ed. in English) · 2017Review
- Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.Journal of the American Chemical Society · 2017Article
- Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.Journal of the American Chemical Society · 2017Article
- Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.Topics in current chemistry (Cham) · 2016Review
- Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.Chemical communications (Cambridge, England) · 2016Article
- Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines.Angewandte Chemie (International ed. in English) · 2016Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The cationic ruthenium catalyst generated upon the acid-base reaction of H2Ru(CO)(PPh3)3 and 2,4,6-(2-Pr)3PhSO3H promotes the redox-triggered C-C coupling of 2-alkynes and primary alcohols to form (Z)-homoallylic alcohols with good to complete control of olefin geometry. Deuterium labeling studies, which reveal roughly equal isotopic compositions at the allylic and distal vinylic positions, along with other data, corroborate a catalytic mechanism involving ruthenium(0)-mediated allene-aldehyde oxidative coupling to form a transient oxaruthenacycle, an event that ultimately defines (Z)-olefin stereochemistry.
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