2020
DOI: 10.1002/ajoc.202000154
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Synthesis of Bio‐Based Cyclic Carbonates Using a Bio‐Based Hydrogen Bond Donor: Application of Ascorbic Acid to the Cycloaddition of CO2 to Oleochemicals

Abstract: Oleochemicals such as functionalized fatty acid esters and vegetable oils are classes of renewably sourced compounds that are increasingly attracting attention in sustainable chemistry as replacement for fossil-fuel based chemicals. The possibility of coupling CO 2 with epoxidized fatty acids esters (EFAEs) and epoxidized vegetable oils (EVOs) to afford compounds that are attractive as additives or chemical intermediates in the synthesis of non-isocyanate polyhydroxyurethanes (NIPU) can conjugate highly sought… Show more

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Cited by 50 publications
(54 citation statements)
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“…Among the catalysts, simple and readily available L-ascorbic acid 14/TBAC allowed the synthesis of the cis-iCFA1 from cis-iEFA1 with high diastereoselectivity (cis : trans = 85 : 15). 231 The system 14/TBAC showed (expectedly) lower substrate conversion than 14/TBAB and 14/TBAI but higher chemoselectivity towards cis-iCFA1 (>99%), whereas in the other two cases a significant amount of the side products were formed (entry 3). When 13/TBAI or 14/TBAI were selected as catalysts, trans-iCFA1 was observed as the main carbonate product (entries 1 and 3), whereas iCFA1 was preferentially formed when utilizing bifunctional catalyst 15 regardless of the nature of the halide (entry 4) though with the lowest stereocontrol towards cis-iCFA1 in the presence of iodide.…”
Section: Internal Carbonates From Efa Derivativesmentioning
confidence: 97%
“…Among the catalysts, simple and readily available L-ascorbic acid 14/TBAC allowed the synthesis of the cis-iCFA1 from cis-iEFA1 with high diastereoselectivity (cis : trans = 85 : 15). 231 The system 14/TBAC showed (expectedly) lower substrate conversion than 14/TBAB and 14/TBAI but higher chemoselectivity towards cis-iCFA1 (>99%), whereas in the other two cases a significant amount of the side products were formed (entry 3). When 13/TBAI or 14/TBAI were selected as catalysts, trans-iCFA1 was observed as the main carbonate product (entries 1 and 3), whereas iCFA1 was preferentially formed when utilizing bifunctional catalyst 15 regardless of the nature of the halide (entry 4) though with the lowest stereocontrol towards cis-iCFA1 in the presence of iodide.…”
Section: Internal Carbonates From Efa Derivativesmentioning
confidence: 97%
“…Although phenolic phosphonium salts catalyzed this transformation without needing a co‐catalyst, they required longer reaction times [12d] . Finally, the recently reported ascorbic acid/TBAC catalyst system catalyzed the preparation of the cyclic carbonate product in an excellent yield (85 %) at lower reaction pressure, though it required 48 hours and higher reaction temperature (Table 4, entry 10) [12f] …”
Section: Resultsmentioning
confidence: 99%
“…However, the use of an iodide anion as nucleophile source produced the trans isomer as the major product (Table 3, entry 3). It is worth mentioning that allyl alcohol by‐product 8 was obtained as a side product when PPNCl was used as co‐catalyst (Figure S53; Table 3, entries 4, 6 and 8) due to the rearrangement of the epoxide functionality [11d,12e,f] …”
Section: Resultsmentioning
confidence: 99%
“…63 generally show the formation of signals relative to the cyclic carbonate products in the 4-5 ppm region and the disappearance of the signals relative to the epoxide substrates in the 2-3 ppm region [7] , [8] , [9] . These data are useful to estimate the conversion of epoxides and to calculate conversion values based on the integration of corresponding signals of products and epoxides [10] , [11] , [12] . These data generally confirm the complete or nearly complete conversion of epoxide substrates and the absence of evident reaction by-products and the reproducible application of the catalysts…”
Section: Data Descriptionmentioning
confidence: 99%