A switchable domino process for the construction of novel CO2- sourced sulfur-containing building blocks and polymers

Ouhib, Farid; Grignard, Bruno; Van den Broeck, Elias; Luxen, André; Robeyns, Koen; Van Speybroeck, Véronique; Jérôme, Christine; Detrembleur, Christophe

doi:10.1002/anie.201905969

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Article (Scientific journals)

A switchable domino process for the construction of novel CO2- sourced sulfur-containing building blocks and polymers

Ouhib, Farid; Grignard, Bruno; Van den Broeck, Elias et al.

2019 • In Angewandte Chemie International Edition, 58 (34), p. 11768-11773

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/237090

DOI
10.1002/anie.201905969

PubMed
31216118

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Keywords :

supercritical carbon dioxide; cyclic carbonate; step-growth polymerization

Abstract :

[en] alpha-alkylidene cyclic carbonates (aCCs) recently emerged as attractive CO2-sourced synthons for the construction of complex organic molecules. Herein, we report the transformation of aCCs into novel families of sulfur-containing compounds by organocatalyzed chemoselective addition of thiols, following a domino process that is switched on/off depending on the desired product. The process is extremely fast, versatile in substrate scope, provides selectively linear thiocarbonates or elusive tetrasubstituted ethylene carbonates with high yields following a 100% atom economy reaction, and valorizes CO2 as a renewable feedstock. It is also exploited to produce a large diversity of unprecedented functional polymers. It constitutes a robust platform for the design of new sulfur-containing organic synthons and important families of polymers.

Research Center/Unit :

CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
Center for Education and Research on Macromolecules (CERM), Belgium

Disciplines :

Chemistry
Materials science & engineering

Author, co-author :

Ouhib, Farid ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Grignard, Bruno ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Van den Broeck, Elias; Ghent University, Center for Molecular Modeling, Belgium > ,

Luxen, André ; Univeristy of Liège (ULiège), GIGA – CRC in vivo Imaging, Belgium

Robeyns, Koen; Université Catholique de Louvain (UCL), Institute of Condensed Matter and Nanosciences (IMCN), Belgium

Van Speybroeck, Véronique; Ghent University, Center for Molecular Modeling, Belgium

Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium

Language :

English

Title :

A switchable domino process for the construction of novel CO2- sourced sulfur-containing building blocks and polymers

Publication date :

19 August 2019

Journal title :

Angewandte Chemie International Edition

ISSN :

1433-7851

eISSN :

1521-3773

Publisher :

Wiley, Weinheim, Germany

Volume :

Issue :

Pages :

11768-11773

Peer reviewed :

Peer Reviewed verified by ORBi

Name of the research project :

The Excellence of Science (EOS) Program in the frame of the NECOPOL Project

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
EOS - The Excellence Of Science Program

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since 20 June 2019

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Bibliography

J. Zhang, J. Yang, T. Dong, M. Zhang, J. Chai, S. Dong, T. Wu, X. Zhou, G. Cu, Small 2018, 14, 1800821;
J. Mindemark, M. J. Lacey, T. Bowden, D. Brandell, Prog. Polym. Sci. 2018, 81, 114–143;
M. I. Childers, J. M. Longo, N. J. Van Zee, A. M. LaPointe, G. W. Coates, Chem. Rev. 2014, 114, 8129–8152;
S. J. Poland, D. J. Darensbourg, Green Chem. 2017, 19, 4990–5011;
L. Maisonneuve, O. Lamarzelle, E. Rix, E. Grau, H. Cramail, Chem. Rev. 2015, 115, 12407–12439.
M. Alves, B. Grignard, R. Mereau, C. Jerome, T. Tassaing, C. Detrembleur, Catal. Sci. Technol. 2017, 7, 2651–2684;
G. Fiorani, W. Guo, A. W. Kleij, Green Chem. 2015, 17, 1375–1389;
C. Martín, G. Fiorani, A. W. Kleij, ACS Catal. 2015, 5, 1353–1370;
H. Büttner, L. Longwitz, J. Steinbauer, T. Werner, Top. Curr. Chem. 2017, 375, 1–56,
S. Dabral, T. Schaub, Adv. Synth. Catal. 2019, 361, 223–246.
J. E. Gómez, A. W. Kleij, Curr. Opin. Green Sust. Chem. 2017, 3, 55–60.
W. Guo, J. E. Gómez, À. Cristòfol, J. Xie, A. W. Kleij, Angew. Chem. Int. Ed. 2018, 57, 13735–13747;
Angew. Chem. 2018, 130, 13928–13941.
S. Dabral, T. Schaub, Adv. Synth. Catal. 2019, 361, 223–246;
S. Dabral, B. Bayarmagnai, M. Hermsen, J. Schießl, V. Mormul, A. S. K. Hashmi, T. Schaub, Org. Lett. 2019, 21, 1422–1425.
Y.-B. Wang, Y.-M. Wang, W. Zhang, X. Lu, J. Am. Chem. Soc. 2013, 135, 11996–12003;
Y. Kayaki, M. Yamamoto, T. Ikariya, Angew. Chem. Int. Ed. 2009, 48, 4194–4197;
Angew. Chem. 2009, 121, 4258–4261;
A. Boyaval, R. Mereau, B. Grignard, C. Detrembleur, C. Jerome, T. Tassaing, ChemSusChem 2017, 10, 1241–1248;
R. Méreau, B. Grignard, A. Boyaval, C. Detrembleur, C. Jerome, T. Tassaing, ChemCatChem 2018, 10, 956–960;
Y. Wu, Y. Zhao, R. Li, B. Yu, Y. Chen, X. Liu, C. Wu, X. Luo, Z. Liu, ACS Catal. 2017, 7, 6251–6255;
Y. Yuan, Y. Xie, C. Zeng, D. Song, S. Chaemchuen, C. Chen, F. Verpoort, Green Chem. 2017, 19, 2936–2940;
B. Grignard, C. Ngassamtounzoua, S. Gennen, B. Gilbert, R. Mereau, C. Jerome, T. Tassaing, C. Detrembleur, ChemCatChem 2018, 10, 2584–2592;
J. Hu, J. Ma, Q. Zhu, Q. Qian, H. Han, Q. Mei, B. Han, Green Chem. 2016, 18, 382–385;
S.-L. Hou, J. Dong, X.-L. Jiang, Z.-H. Jiao, B. Zhao, Angew. Chem. Int. Ed. 2019, 58, 577–581;
Angew. Chem. 2019, 131, 587–591.
C.-R. Qi, H.-F. Jiang, Green Chem. 2007, 9, 1284–1286;
P. Toullec, A. Martin, M. Gio-Batta, C. Bruneau, P. Dixneuf, Tetrahedron Lett. 2000, 41, 5527–5531;
Z.-H. Zhou, Q.-W. Song, L.-N. He, ACS Omega 2017, 2, 337–345;
Q.-W. Song, Z.-H. Zhou, M.-Y. Wang, K. Zhang, P. Liu, J.-Y. Xun, L.-N. He, ChemSusChem 2016, 9, 2054–2058;
Y. Zhao, Z. Yang, B. Yu, H. Zhang, H. Xu, L. Hao, B. Han, Z. Liu, Chem. Sci. 2015, 6, 2297–2301;
N. B. Chernysheva, A. A. Bogolyubov, V. V. Semenov, Chem. Heterocycl. Compd. 2003, 39, 1057–1064.
S. Gennen, B. Grignard, T. Tassaing, C. Jérôme, C. Detrembleur, Angew. Chem. Int. Ed. 2017, 56, 10394–10398;
Angew. Chem. 2017, 129, 10530–10534.
P. Chauhan, S. Mahajan, D. Enders, Chem. Rev. 2014, 114, 8807–8864.
W. T. Wiesler, M. H. Caruthers, J. Org. Chem. 1996, 61, 4272–4281;
K. Arai, T. Wirth, Org. Process Res. Dev. 2014, 18, 1377–1381.
L.-F. Hu, Y. Li, B. Liu, Y.-Y. Zhang, X.-H. Zhang, RSC Adv. 2017, 7, 49490–49497;
M. Luo, X. H. Zhang, B. Y. Du, Q. Wang, Z. Q. Fan, Polym. Chem. 2015, 6, 4978–4983;
H.-B. Cao, M.-J. Shen, L.-H. Chen, Sichuan Ligong Xueyuan Xuebao Ziran Kexueban 2013, 26, 1–5.
K. R. Henke, Water Environ. Res. 1998, 70, 1178–1185;
M. Matlock, K. R. Henke, D. A. Atwood, J. Hazard. Mater. 2002, 92, 129–142.
B. Liu, X. Zhang, Gen. Chem. 2018, 4, 180007.
Y. Li, H.-Y. Duan, M. Luo, Y.-Y. Zhang, X.-H. Zhang, D. J. Darensbourg, Macromolecules 2017, 50, 8426–8437;
M. Luo, X.-H. Zhang, D. J. Darensbourg, Acc. Chem. Res. 2016, 49, 2209–2219;
T.-J. Yue, W.-M. Ren, L. Chen, G.-G. Gu, Y. Liu, X.-B. Lu, Angew. Chem. Int. Ed. 2018, 57, 12670–12674;
Angew. Chem. 2018, 130, 12852–12856.