Sangon, Suwiwat, Supanchaiyamat, Nontipa, Sherwood, James Richard orcid.org/0000-0001-5431-2032 et al. (2 more authors) (2020) Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in carbon–carbon bond formation. Reaction Chemistry & Engineering. pp. 1798-1804. ISSN 2058-9883
Abstract
There is a lot of interest in the development of new, safer and more sustainable polar aprotic solvents due to their importance in industrial applications and significant safety issues with the most commonly used examples. One such area of application is in pharmaceutically relevant C–C coupling reactions, where polar aprotic solvents are commonly used for solubility and to stabilise reaction intermediates. Although there are now a number of excellent alternatives in the literature, to date they have not been compared in a single study. This study demonstrates the effectiveness of the green solvents N-butylpyrrolidinone (NBP), γ-valerolactone (GVL), propylene carbonate (PC) and dihydrolevoglucosenone (Cyrene) in Heck and Baylis–Hillman reactions. Good conversions and initial rates were observed in GVL and NBP in Heck reactions. Cyrene exhibited high initial rates of reaction and high yields in the Baylis–Hillman reaction. This demonstrates Cyrene to be a promising alternative polar aprotic solvent for this reaction.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Royal Society of Chemistry 2020. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 05 Oct 2020 09:00 |
Last Modified: | 02 Apr 2025 23:19 |
Published Version: | https://doi.org/10.1039/D0RE00174K |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/D0RE00174K |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:166326 |
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Description: 10 Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in coupling reactions