Electrochemical Incorporation of Electrophiles into the Biomass-Derived Platform Molecule 5-(Chloromethyl)furfural.
5-(chloromethyl)furfural
biobased products
carbon dioxide fixation
electrochemistry
electrosynthesis
platform molecules
Journal
ChemSusChem
ISSN: 1864-564X
Titre abrégé: ChemSusChem
Pays: Germany
ID NLM: 101319536
Informations de publication
Date de publication:
08 Mar 2023
08 Mar 2023
Historique:
revised:
15
12
2022
received:
19
09
2022
pubmed:
17
12
2022
medline:
17
12
2022
entrez:
16
12
2022
Statut:
ppublish
Résumé
The 5-(chloromethyl)furfural (CMF) derivative ethyl 5-(chloromethyl)furan-2-carboxylate undergoes two-electron electrochemical reduction in a simple, undivided cell to give the corresponding furylogous enolate anion, which can either be quenched with carbon dioxide to give a 5-(carboxymethyl)furan-2-carboxylate or with hydrogen ion to give a 5-methylfuran-2-carboxylate, thereby expanding the derivative scope of CMF as a biobased platform molecule.
Identifiants
pubmed: 36525531
doi: 10.1002/cssc.202201787
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202201787Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
M. Mascal, ChemSusChem 2015, 8, 3391-3395.
M. Mascal, ACS Sustainable Chem. Eng. 2019, 7, 5588-5601.
M. Mascal, S. Dutta, Fuel Process. Technol. 2020, 197, 106192.
A. Little, A. Pellis, J. W. Comerford, E. Naranjo-Valles, N. Hafezi, M. Mascal, T. J. Farmer, ACS Sustainable Chem. Eng. 2020, 8, 14471-14483.
J. Saska, Z. Li, A. L. Otsuki, J. Wei, J. C. Fettinger, M. Mascal, Angew. Chem. Int. Ed. 2019, 58, 17293-17296;
Angew. Chem. 2019, 131, 17453-17456.
M. Mascal, S. Dutta, Green Chem. 2011, 13, 40-41.
M. Mascal, S. Dutta, Green Chem. 2011, 13, 3101-3102.
F. Chang, S. Dutta, J. J. Becnel, A. S. Estep, M. Mascal, J. Agric. Food Chem. 2014, 62, 476-480.
B. Chen, Z. Li, Y. Feng, W. Hao, Y. Sun, X. Tang, X. Zeng, L. Lin, ChemSusChem 2021, 14, 847-851.
H. Miao, N. Shevchenko, A. L. Otsuki, M. Mascal, ChemSusChem 2021, 14, 303-305.
https://xftechnologies.com/platform-chemistry.
X.-F. Liu, K. Zhang, L. Tao, X.-B. Lu, W.-Z. Zhang, Green Chem. Eng. 2022, 3, 125-137.
Z. Yang, Y. Yu, L. Lai, L. Zhou, K. Ye, F.-E. Chen, Green Synth. Catal. 2021, 2, 19-26.
H. Senboku, K. Nagakura, T. Fukuhara, S. Hara, Tetrahedron 2015, 71, 3850-3856.
N. Corbin, D.-T. Yang, N. Lazouski, K. Steinberg, K. Manthiram, Chem. Sci. 2021, 12, 12365-12376.
United States Environmental Protection Agency, Aluminum: Material-Specific Data. Retrieved from https://www.epa.gov/facts-and-figures-about-materials-waste-and-recycling/aluminum-material-specific-data#AluminumTableandGraph.
S. Dutta, L. Wu, M. Mascal, Green Chem. 2015, 17, 3737-3739.
S. Rondinini, P. R. Mussini, P. Muttini, G. Sello, Electrochim. Acta 2001, 46, 3245-3258.
M. D. Otero, B. Batanero, F. Barba, Tetrahedron Lett. 2006, 47, 2171-2173.
S. Wang, T. Feng, Y. Wang, Y. Qiu, Chem. Asian J. 2022, e202200543.
H. Miao, H. Ling, N. Shevchenko, M. Mascal, Organometallics 2021, 40, 3952-3957.
K. Scott, Renewable and Sustainable Energy Reviews 2018, 81, 1406-1426.
W. Farone, M. Fatigati, Michael, PCT Int. Appl. 2019, WO 2019118704 A1.
W. Yu, Y. Alencar Marques, L. Havens, S. B. Klamo, PCT Int. Appl. 2021, WO 2021211218 A1.