Synthesis of ureas in the bio-alternative solvent Cyrene

Mistry, Liam; Mapesa, Kopano; Bousfield, Thomas W.; Camp, J. E.

doi:10.1039/c7gc00908a

Cited by 79 publications

(54 citation statements)

References 65 publications

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“…While it remains to be seen whether Cyrene is a viable replacement for other industrial solvents, the overall market for pharmaceutical and specialty solvents represents 900 kton/yr and is growing at 4%/yr . Cyrene has been evaluated successfully as a solvent in a wide range of applications, including fluorination, C‐C bond formation (e.g., Menschutkin reaction, Sonogashira cross‐coupling, and Cacchi‐type annulations), urea synthesis, and MOF synthesis . Cyrene has also been demonstrated as a solvent for nanomaterials synthesis, for example in delaminating graphite into graphene, which was independently reported by Salavagione et al and Gharib et al…”

Section: Products From C6 (Lgo and Hmf)mentioning

confidence: 90%

Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocycles

et al. 2018

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Section: Products From C6 (Lgo and Hmf)mentioning

confidence: 90%

Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocycles

et al. 2018

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“…Camp and co-workers showedthat the reaction of aryl isocyanates 37 with secondary amines 38 gave the desired ureas 39 in good to excellent yields when Cyrene was used as the solvent (Scheme 9). [52] An in situ 19 FNMR spectroscopy investigation showedt hat the reaction proceeded at similar rates in Cyrene, DMF,a nd CH 2 Cl 2 . Importantly,t reating the reaction mixture with water resulted in product precipitation and the Cyrene could be separated from the product without any furtherw orkup.T he resulting Scheme5.Hydration of Cyrene (2)and LGO (1)derivatives.…”

Section: Use Of Cyrene As Abio-available Solventmentioning

confidence: 97%

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

2018

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The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class of solvents is the dipolar aprotics, which include N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP). In addition to being derived from non-renewable resources, these solvents are also under increased regulatory pressures that will limit their industrial applications. This Concept concerns the bio-available solvent Cyrene (dihydrolevoglucosenone) as a potential replacement for toxic dipolar aprotic solvents. An emphasis is placed on examining the strengths and weaknesses of Cyrene as a solvent and is accomplished by looking at the synthesis, derivatization, and application in synthetic protocols of Cyrene. With respect to the Twelve Principles of Green Chemistry, this Concept describes a bio-available solvent that should have a disruptive effect on the use of traditional industrial dipolar aprotic solvents.

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“…Cyrene has previously demonstrated successful application in materials chemistry, 41,42 in addition to synthetic organic transformations. [43][44][45] Based on our interest in solvent replacement strategies, 21,[46][47][48][49] we are pleased to report the use of Cyrene as a bio-based solvent in amide bond formation.…”

Section: -40mentioning

confidence: 99%

Cyrene as a bio-based solvent for HATU mediated amide coupling

et al. 2018

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Amide bonds are one of the underpinning linkages in all living systems and are fundamental within drug discovery. Current methods towards their synthesis frequently rely on the use of dipolar aprotic solvents; however, due to increasingly stringent regulations and growing societal pressures, safe and more sustainable alternatives are highly sought after. Herein, we evaluate the application of the bio-based solvent Cyrene™ in the HATU mediated synthesis of amides and peptides. We found that Cyrene functioned as a competent replacement for DMF in the synthesis of a series of lead-like compounds and dipeptides (25 examples, 63-100%).

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Synthesis of ureas in the bio-alternative solvent Cyrene

Cited by 79 publications

References 65 publications

Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocycles

Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocycles

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

Cyrene as a bio-based solvent for HATU mediated amide coupling

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