TY - JOUR
T1 - Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts
AU - Fan, Yang
AU - Tiffner, Maximilian
AU - Schörgenhumer, Johannes
AU - Robiette, Raphaël
AU - Waser, Mario
AU - Kass, Steven R.
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/9/7
Y1 - 2018/9/7
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.8b01374
DO - 10.1021/acs.joc.8b01374
M3 - Article
C2 - 30020780
AN - SCOPUS:85050341782
SN - 0022-3263
VL - 83
SP - 9991
EP - 10000
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -