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

The Journal of Organic Chemistry
Yang FanSteven R Kass

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.

References

Feb 17, 1994·Nature·K C NicolaouK Paulvannan
May 9, 1996·Chemical Reviews·Abbas-Alli G. Shaikh, Swaminathan Sivaram
Oct 1, 1996·Chemical Reviews·Dorothy H. Gibson
Sep 18, 2002·Accounts of Chemical Research·Pietro Tundo, Maurizio Selva
Sep 18, 2002·Accounts of Chemical Research·Walter Leitner
May 13, 2003·Chemical Communications : Chem Comm·Hajime KawanamiYutaka Ikushima
Mar 25, 2004·Journal of the American Chemical Society·Xiao-Bing LuRong Zhang
Jun 15, 2007·Chemical Reviews·Toshiyasu SakakuraHiroyuki Yasuda
Jul 5, 2007·Angewandte Chemie·Jerome BayardonArmin Börner
Jul 12, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Michele Aresta, Angela Dibenedetto
Nov 6, 2008·ChemSusChem·Kai Man Kerry YuShik Chi Edman Tsang
Mar 5, 2009·Chemical Communications : Chem Comm·Toshiyasu Sakakura, Kazufumi Kohno
Mar 30, 2010·Chemical Reviews·Benjamin SchäffnerArmin Börner
Apr 10, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Siti Nurhanna Riduan, Yugen Zhang
May 4, 2010·Chemistry : a European Journal·William CleggRiccardo Pasquale
Jun 3, 2010·Journal of the American Chemical Society·Samantha L RichesVarinder K Aggarwal
Jul 24, 2010·Angewandte Chemie·Deanna M D'AlessandroJeffrey R Long
Sep 17, 2011·ChemSusChem·Elsje Alessandra QuadrelliSiglinda Perathoner
Jan 11, 2013·Journal of the American Chemical Society·Christopher J WhiteoakArjan W Kleij
Feb 5, 2013·Chemical Communications : Chem Comm·Michael A BertucciMichel R Gagné
Nov 22, 2013·Journal of the American Chemical Society·Jennifer A KozakTimothy F Jamison
Dec 10, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Richard G TordeShane M Lamos
Aug 27, 2014·Chemistry : a European Journal·Yingying SongHuanwang Jing
Oct 21, 2014·ChemSusChem·Andrea M Hardman-Baldwin, Anita E Mattson
Aug 18, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Dan ZhaoWei-Yin Sun

❮ Previous
Next ❯

Citations

Oct 9, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Hongmei WangLei Li
Mar 21, 2020·Organic & Biomolecular Chemistry·Céline SperandioAdrien Quintard
Jul 25, 2019·Journal of the American Society for Mass Spectrometry·Yunfeng ChaiChengyin Lu
Oct 24, 2018·The Journal of Organic Chemistry·Ivor SmajlagicTravis Dudding
Dec 4, 2019·The Journal of Organic Chemistry·Ivor SmajlagicTravis Dudding

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.