2011
DOI: 10.1021/op200234j
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Catalytic Hydrogenation of Esters. Development of an Efficient Catalyst and Processes for Synthesising (R)-1,2-Propanediol and 2-(l-Menthoxy)ethanol

Abstract: A ruthenium catalyst for the reduction of esters by hydrogenation has been developed. Processes for the hydrogenation of esters have also been developed for (R)-1,2-propanediol and 2-(l-menthoxy)ethanol. The catalyst shows good catalytic activity for the hydrogenation of esters in methanol. Methyl lactate was reduced at 30 °C and gave turnover numbers (TON) up to 4000. The optical purity of the (R)-1,2-propanediol made by the hydrogenation of methyl (R)-lactate was higher than that via the asymmetric hydrogena… Show more

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Cited by 287 publications
(256 citation statements)
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“…As proposed by Kuriyama et al, we also surmise that in the presence of CO, an equilibrium between the monocarbonyl RuH(CO)(HN(CH 2 CH 2 PPh 2 ) 2 ) + and dicarbonyl complex, RuH(CO) 2 (HN(CH 2 CH 2 PPh 2 ) 2 ) + is possible . 22 Therefore, RuH(CO) 2 (HN(CH 2 CH 2 PPh 2 ) 2 ) + is probably the resting state of the catalytic cycle. Interestingly, although PEHA can act as potential multidentate nitrogen donor ligand to the Ru center, no ligand exchange occurred under the reaction conditions, as evidenced by the absence of free PNP ligand signal in 31 P NMR.…”
Section: Table 2 Extended-time Study At 145 and 125 °Cmentioning
confidence: 99%
“…As proposed by Kuriyama et al, we also surmise that in the presence of CO, an equilibrium between the monocarbonyl RuH(CO)(HN(CH 2 CH 2 PPh 2 ) 2 ) + and dicarbonyl complex, RuH(CO) 2 (HN(CH 2 CH 2 PPh 2 ) 2 ) + is possible . 22 Therefore, RuH(CO) 2 (HN(CH 2 CH 2 PPh 2 ) 2 ) + is probably the resting state of the catalytic cycle. Interestingly, although PEHA can act as potential multidentate nitrogen donor ligand to the Ru center, no ligand exchange occurred under the reaction conditions, as evidenced by the absence of free PNP ligand signal in 31 P NMR.…”
Section: Table 2 Extended-time Study At 145 and 125 °Cmentioning
confidence: 99%
“…Note that the welld escribed Ru-MACHO-BH catalyst does not facilitate the homogeneous hydrogenation of substrate 4n to 5n. [10] Thev ersatility of complex 3 as efficienta nd selective homogeneoush ydrogenation catalyst was further demonstrated in the preparation of diols from diesters and lactones, respectively.A romatic diesters such as dimethylt erephthalate (4o)a nd naphthalene 2,6-dimethylc arboxylate (4p)w ere cleanly reduced to form the diols in good yields.I nterestingly,t he catalytic systemi st olerant towards the pyridine ring in compound 4q and almost quantitative product formation was observedu ponr eactionw ith H 2 gas (Table 3, entry 3). Comparable results were found with the aliphatic dimethyls uccinate (Table 3, entry 4).…”
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confidence: 99%
“…[4] In the early 2000s av ariety of seminal reportso n homogeneous catalysts for the hydrogenation of estersa ppeared in the literature. [5][6][7] Major developments in this field were madeb yt he groups of Milstein, [8] Saudan, [9] Kuriyama, [10] andG usev. [11] In addition, very recently ah ighly active bis-NHC amino pincerR uc omplexh as been developed for ester hydrogenation.…”
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confidence: 99%
“…I should note that by the time we had got round to publish these improved protocols, a number of interesting ester hydrogenation catalysts had appeared, many of which use (different) tridentate ligands including an amine function. 22,39,40 Takasago International Corporation have recently reported a ton-scale ester hydrogenation using a new ruthenium-PNP catalyst. 40 We will soon report several related catalysts that work pretty well, but we also believe the scope and application of ester hydrogenation needs to be fully studied, so that the synthetic community adopt this greener reaction protocol in target synthesis.…”
Section: Figurementioning
confidence: 99%