Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts

Yang Fan, Maximilian Tiffner, Johannes Schörgenhumer, Raphaël Robiette, Mario Waser, Steven R Kass

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)9991-10000
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number17
DOIs
StatePublished - Sep 7 2018

PubMed: MeSH publication types

  • Journal Article

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