Ru3(CO)12/1,10-phenanthroline-catalyzed hydroformylation of styrene and acrylic esters |
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| Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Department of Crystallography, St. Petersburg State University, 199034 St. Petersburg, Russian Federation;3. I. M. Gubkin Russian State University of Oil and Gas, 119991 Moscow, Russian Federation;1. CQC, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal;2. Luzitin SA, Edificio Bluepharma, S. Martinho do Bispo, 3045-016 Coimbra, Portugal;3. Faculty of Pharmacy, Exact Sciences and Technology Unit, State University of Goiás, 75132400 Anápolis, Goiás, Brazil;1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, PR China;2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China |
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| Abstract: | The Ru3(CO)12/1,10-phenanthroline-catalyzed hydroformylation of styrene under 100 atm of syngas (CO:H2=1:1) at 120°C in DMF gives the corresponding branched and linear aldehydes in 58 and 22% yields, respectively. With the use of quinuclidine as a ligand in place of 1,10-phenanthroline in N,N-dimethylacetamide, the corresponding branched and linear oxo-alcohols were obtained in 53 and 28% yields, respectively. Hydroformylation of methyl acrylate by a catalyst system of Ru3(CO)12/1,10-phenanthroline to afford 4-methoxy-4-methyl-δ-valerolactone 1 in 31% yield, while the catalyst system of Ru3(CO)12/PPh3 yields the open-chain aldehyde, dimethyl 2-formyl-2-methylglutarate (3), which is the precursor of lactone 1 in 18% yield. |
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