Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts
(2018) The Journal of Organic Chemistry — Vol. 83, n° 17, p. 9991-10000 (2018)
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- Authors
Kass, Steven R. 
- Abstract
- Cycloadditions of epoxides with CO2 to synthesize cyclic five-membered ring organic carbonates are of broad interest from a synthetic, environmental, and green chemistry perspective, and the development of effective catalysts for these transformations is an ongoing challenge. A series of eight charge-containing thiourea salts that catalyze these reactions under mild conditions (i.e., 60 °C and atmospheric CO2 pressure) are reported. Substrate scope and mechanistic studies were also carried out, isotope effects were measured, and a reactive intermediate was isolated revealing a surprising pathway in which a thiourea catalyst serves as a nucleophile in the cleavage of the epoxide ring.
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Citations
Fan, Y., Tiffner, M., Schörgenhumer, J., Robiette, R., Waser, M., & Kass, S. R. (2018). Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts. The Journal of Organic Chemistry, 83(17), 9991-10000. https://doi.org/10.1021/acs.joc.8b01374 (Original work published 2018)