Atom-economic Approach to the Synthesis of α-(Hetero)aryl-substituted Furan Derivatives from Biomass.
HMF
atom economy
biomass
cycloaddition
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
03 Jan 2022
03 Jan 2022
Historique:
revised:
18
11
2021
received:
26
10
2021
pubmed:
23
11
2021
medline:
23
11
2021
entrez:
22
11
2021
Statut:
ppublish
Résumé
An atom-economic ring construction approach to the synthesis of α-(hetero)arylfurans based on renewable furanic platform chemicals has been developed. Corresponding compounds have been prepared in good to excellent yields via [2+2+2] and [4+2] cycloaddition reactions using metal-catalyzed or photoredox protocols. Easily available HMF-based 2-hydroxymethyl-5-ethynylfuran and 2-hydroxymethyl-5-cyanofuran were used as starting materials. A synthetic route with an improved carbon economy factor has been implemented to achieve sustainability aim. The possible application of arylfurans as molecular conductors has been investigated by DFT calculations, which revealed excellent charge transfer properties. As a future perspective, integration of biomass processing strategy into manufacturing of molecular electronics was pointed out to achieve the aim of sustainability.
Identifiants
pubmed: 34807522
doi: 10.1002/asia.202101227
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202101227Subventions
Organisme : Russian Science Foundation
ID : 20-73-00117
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
J. J. Bozell, G. R. Petersen, Green Chem. 2010, 12, 539-554.
R. A. Sheldon, Green Chem. 2014, 16, 950-963.
E. A. Khokhlova, V. V. Kachala, V. P. Ananikov, ChemSusChem 2012, 5, 783-789.
O. H. Pardo Cuervo, S. P. Simeonov, A. F. Peixoto, M. D. Popova, H. I. Lazarova, G. P. Romanelli, J. J. Martínez, C. Freire, C. A. M. Afonso, Energy Technol. 2019, 7, 1900780.
A. G. Sathicq, M. Annatelli, I. Abdullah, G. Romanelli, F. Aricò, Sustain. Chem. Pharm. 2021, 19, 100352.
M. Pagliaro, Angew. Chem. Int. Ed. 2019, 58, 11154-11159;
Angew. Chem. 2019, 131, 11272-11277.
R. F. A. Gomes, J. M. J. M. Ravasco, ChemSusChem 2021, 14, 3047-3053.
C. Thoma, J. Konnerth, W. Sailer-Kronlachner, T. Rosenau, A. Potthast, P. Solt, H. W. G. van Herwijnen, ChemSusChem 2020, 13, 5408-5422.
K. I. Galkin, V. P. Ananikov, ChemSusChem 2019, 12, 2976-2982.
F. A. Kucherov, L. V. Romashov, K. I. Galkin, V. P. Ananikov, ACS Sustainable Chem. Eng. 2018, 6, 8064-8092.
A. S. Amarasekara, in Renewable Polymers, John Wiley & Sons, Inc., 2011, pp. 381-428.
P. C. A. Bruijnincx, Y. Roman-Leshkov, Catal. Sci. Technol. 2014, 4, 2180-2181.
V. M. Chernyshev, O. A. Kravchenko, V. P. Ananikov, Russ. Chem. Rev. 2017, 86, 357-387.
H. Zhu, W. Luo, P. N. Ciesielski, Z. Fang, J. Y. Zhu, G. Henriksson, M. E. Himmel, L. Hu, Chem. Rev. 2016, 116, 9305-9374.
L. Wu, T. Moteki, A. A. Gokhale, D. W. Flaherty, F. D. Toste, Chem 2016, 1, 32-58.
K. S. Kozlov, L. V. Romashov, V. P. Ananikov, Green Chem. 2019, 21, 3464-3468.
A. Al Ghatta, J. D. E. T. Wilton-Ely, J. P. Hallett, Green Chem. 2021, 23, 1716-1733.
R. Ahorsu, F. Medina, M. Constantí, Energies 2018, 11, 3366.
F. Weigang, V. Charlie, Q. Yves, P. Florence, Curr. Org. Synth. 2019, 16, 583-614.
T. Su, D. Zhao, Y. Wang, H. Lü, R. S. Varma, C. Len, ChemSusChem 2021, 14, 266-280.
Q. Hou, X. Qi, M. Zhen, H. Qian, Y. Nie, C. Bai, S. Zhang, X. Bai, M. Ju, Green Chem. 2021, 23, 119-231.
J. M. J. M. Ravasco, C. M. Monteiro, F. Siopa, A. F. Trindade, J. Oble, G. Poli, S. P. Simeonov, C. A. M. Afonso, ChemSusChem 2019, 12, 4629-4635.
A. Tampieri, C. Russo, R. Marotta, M. Constantí, S. Contreras, F. Medina, Appl. Catal. B 2021, 282, 119599.
W. Fan, Y. Queneau, F. Popowycz, Green Chem. 2018, 20, 485-492.
B. Y. Karlinskii, A. Y. Kostyukovich, F. A. Kucherov, K. I. Galkin, K. S. Kozlov, V. P. Ananikov, ACS Catal. 2020, 10, 11466-11480.
X. Huang, J. Song, M. Hua, B. Chen, Z. Xie, H. Liu, Z. Zhang, Q. Meng, B. Han, Chem. Sci. 2021, 12, 6342-6349.
J. Engel, A. Kleemann, B. Kutscher, D. Reichert, Pharmaceutical Substances, 5th ed., Georg Thieme Verlag, Stuttgart, New York, 2009.
D. J. Brooks, S. Papapetropoulos, F. Vandenhende, D. Tomic, P. He, A. Coppell, G. O′Neill, Clin. Neuropharmacol. 2010, 33, 55-60.
N. Szabo, Z. T. Kincses, L. Vecsei, Expert Opin. Drug Metab. Toxicol. 2011, 7, 441-455.
R. B. de Oliveira, E. M. de Souza-Fagundes, H. A. J. Siqueira, R. S. Leite, C. L. Donnici, C. L. Zani, Eur. J. Med. Chem. 2006, 41, 756-760.
B. Masereel, L. Pochet, D. Laeckmann, Eur. J. Med. Chem. 2003, 38, 547-554.
S. Lee, T. Kim, B. H. Lee, S.-e. Yoo, K. Lee, K. Y. Yi, Bioorg. Med. Chem. Lett. 2007, 17, 1291-1295.
S. Lee, K. Y. Yi, S. K. Hwang, B. H. Lee, S.-e. Yoo, K. Lee, J. Med. Chem. 2005, 48, 2882-2891.
S. Rajamaki, A. Innitzer, C. Falciani, C. Tintori, F. Christ, M. Witvrouw, Z. Debyser, S. Massa, M. Botta, Bioorg. Med. Chem. Lett. 2009, 19, 3615-3618.
M. Rinaldi, C. Tintori, L. Franchi, G. Vignaroli, A. Innitzer, S. Massa, J. A. Esté, E. Gonzalo, F. Christ, Z. Debyser, M. Botta, ChemMedChem 2011, 6, 343-352.
A. L. Crowell, C. E. Stephens, A. Kumar, D. W. Boykin, W. E. Secor, Antimicrob. Agents Chemother. 2004, 48, 3602-3605.
J. K. Yano, T. T. Denton, M. A. Cerny, X. Zhang, E. F. Johnson, J. R. Cashman, J. Med. Chem. 2006, 49, 6987-7001.
D. Maiti, A. Halder, A. Sasidharan Pillai, S. De Sarkar, J. Org. Chem. 2021, 22, 16084-16094.
F. Chacón-Huete, D. Mangel, M. Ali, A. Sudano, P. Forgione, ACS Sustainable Chem. Eng. 2017, 5, 7071-7076.
J. M. Quibell, G. Duan, G. J. P. Perry, I. Larrosa, Chem. Commun. 2019, 55, 6445-6448.
G. Huang, L. Lu, H. Jiang, B. Yin, Chem. Comm. 2017, 53, 12217-12220.
G. Huang, B. Yin, Adv. Synth. Catal. 2019, 361, 5576-5586.
R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233.
B. M. Trost, Angew. Chem. Int. Ed. 1995, 34, 259-281;
Angew. Chem. 1995, 107, 285-307.
A. Lapkin, D. J. C. Constable, Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes, Wiley-Blackwell, 2008, p. 344.
L. V. Romashov, V. P. Ananikov, Chem. Asian J. 2017, 12, 2652-2655.
B. Y. Karlinskii, L. V. Romashov, K. I. Galkin, P. G. Kislitsyn, V. P. Ananikov, Synthesis 2019, 51, 1235-1242.
A. Baliani, G. J. Bueno, M. L. Stewart, V. Yardley, R. Brun, M. P. Barrett, I. H. Gilbert, J. Med. Chem. 2005, 48, 5570-5579.
N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, M. Malacria, in Organomet. React., 2007, pp. 1-302.
Y. Shibata, K. Tanaka, Synthesis 2012, 44, 323-350.
C. Song, X. Dong, Z. Wang, K. Liu, C.-W. Chiang, A. Lei, Angew. Chem. Int. Ed. 2019, 58, 12206-12210;
Angew. Chem. 2019, 131, 12334-12338.
D. S. Perekalin, N. V. Shvydkiy, Y. V. Nelyubina, A. R. Kudinov, Mendeleev Commun. 2015, 25, 29-31.
D. S. Perekalin, E. E. Karslyan, E. A. Trifonova, A. I. Konovalov, N. L. Loskutova, Y. V. Nelyubina, A. R. Kudinov, Eur. J. Inorg. Chem. 2013, 2013, 481-493.
H. Chen, J. Fraser Stoddart, Nat. Rev. Mater. 2021, 8, 804-828.
P. T. Mathew, F. Fang, Engineering 2018, 4, 760-771.
D. Xiang, X. Wang, C. Jia, T. Lee, X. Guo, Chem. Rev. 2016, 116, 4318-4440.
H. Oberhofer, K. Reuter, J. Blumberger, Chem. Rev. 2017, 117, 10319-10357.
É. Brémond, M. Savarese, N. Q. Su, Á. J. Pérez-Jiménez, X. Xu, J. C. Sancho-García, C. Adamo, J. Chem. Theory Comput. 2016, 12, 459-465.
É. Brémond, A. Ottochian, Á. J. Pérez-Jiménez, I. Ciofini, G. Scalmani, M. J. Frisch, J. C. Sancho-García, C. Adamo, J. Comput. Chem. 2021, 42, 970-981.
M. Doust Mohammadi, H. Y. Abdullah, ChemistrySelect 2020, 5, 12115-12124.