ArticleThe Journal of organic chemistry2016
Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.
Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 34 citations in OpenAlex.
- Metal-Catalyzed Reductive Coupling of Aryl Halides beyond Premetalated Reagents or Metallic Reductants: Biaryl Formation.Chemical reviews · 2026Review
- Iridium-Catalyzed Stereoselective α-Alkylation of α-Hydroxy Ketones with Minimally Polarized Alkenes.Journal of the American Chemical Society · 2026Article
- β-Substituted Styrenes in Heteroaryl-Directed Hydroalkylative Cross-Couplings: Regio-, Diastereo-, and Enantioselective Formation of β-Stereogenic Tertiary Alcohols.Journal of the American Chemical Society · 2025Article
- Heteroaryl-Directed Iridium-Catalyzed Enantioselective C-H Alkenylations of Secondary Alcohols.Journal of the American Chemical Society · 2025Article
- Historical perspective on ruthenium-catalyzed hydrogen transfer and survey of enantioselective hydrogen auto-transfer processes for the conversion of lower alcohols to higher alcohols.Chemical science · 2022Review
- Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.Journal of the American Chemical Society · 2021Article
- From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.ACS catalysis · 2021Article
- Electroreductive Olefin-Ketone Coupling.Journal of the American Chemical Society · 2020Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct.Journal of the American Chemical Society · 2019Article
- Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.Journal of the American Chemical Society · 2018Article
- Undeca-carbon-yl[(4-methyl-sulfanylphen-yl)di-phenyl-phosphane]triruthenium(0): crystal structure and Hirshfeld surface analysis.Acta crystallographica. Section E, Crystallographic communications · 2018Article
- Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.Angewandte Chemie (International ed. in English) · 2017Article
- Reductive C-C CouplingCurrent opinion in green and sustainable chemistry · 2017Article
- Regioselective Hydrohydroxyalkylation of Styrene with Primary Alcohols or Aldehydes via Ruthenium-Catalyzed C-C Bond Forming Transfer Hydrogenation.Angewandte Chemie (International ed. in English) · 2016Article
- Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.Science (New York, N.Y.) · 2016Review
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4 authors at 1 institution in 1 country.
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Abstract
Osmium(0) complexes derived from Os3(CO)12 and XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) catalyze the C-C coupling of α-hydroxy esters 1a-1i, α-ketols 1j-1o, or 1,2-diols dihydro-1j-1o with ethylene 2a to form ethylated tertiary alcohols 3a-3o. As illustrated in couplings of 1-octene 2b with vicinally dioxygenated reactants 1a, 1b, 1i, 1j, 1k, 1m, higher α-olefins are converted to adducts 4a, 4b, 4i, 4j, 4k, 4m with complete levels of branched regioselectivity. Oxidation level independent C-C coupling is demonstrated by the reaction of 1-octene 2b with diol dihydro-1k, α-ketol 1k, and dione dehydro-1k. Functionalized olefins 2c-2f react with ethyl mandelate 1a to furnish adducts 5a-8a as single regioisomers. The collective data, including deuterium labeling studies, are consistent with a catalytic mechanism involving olefin-dione oxidative coupling to form an oxa-osmacyclopentane, which upon reductive cleavage via hydrogen transfer from the secondary alcohol reactant releases the product of carbinol C-alkylation with regeneration of the ketone. Single-crystal X-ray diffraction data of the dinuclear complex Os2(CO)4(O2CR)2(XPhos)2 and the trinuclear complex Os3(CO)11(XPhos) are reported. These studies suggest increased π-backbonding at the stage of the metal-olefin π-complex plays a critical role in facilitating alkene-carbonyl oxidative coupling, as isostructural ruthenium(0) complexes, which are weaker π-donors, do not catalyze the transformations reported herein.
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