Organocatalytic promoted coupling of carbon dioxide with epoxides: a rational investigation of the cocatalytic activity of various hydrogen bond donors
[en] A catalytic platform based on an onium salt used in combination with organic cocatalysts of various structures was developed for the efficient CO2/epoxide coupling under mild conditions. Through detailed kinetic studies by in-situ FT-IR spectroscopy, a rational investigation of the efficiency of a series of commercially available hydrogen bond donors co-catalysts was realized and the influence of different parameters such as the pressure, the temperature, the catalyst loading, and the nature of the epoxide on the reaction kinetics was evaluated. Fluorinated alcohols were found to be more efficient than other hydrogen bond donor activators proposed previously in the literature under similar conditions.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Alves, Margot ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Grignard, Bruno ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Gennen, Sandro ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Méreau, Raphaël; University of Bordeaux, Institute of Molecular Sciences, France
Detrembleur, Christophe ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Tassaing, Thierry; University of Bordeaux, Institute of Molecular Sciences, France
Language :
English
Title :
Organocatalytic promoted coupling of carbon dioxide with epoxides: a rational investigation of the cocatalytic activity of various hydrogen bond donors
Publication date :
01 September 2015
Journal title :
Catalysis Science and Technology
ISSN :
2044-4753
eISSN :
2044-4761
Publisher :
Royal Society Chemistry
Volume :
5
Issue :
9
Pages :
4636-4643
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
the “Region Wallonne” in the frame of the CO2Green, Sinopliss and Flycoat projects BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture The International Doctoral School IDS-Funmat The "Initiative d’Excellence" (IDEX) program of the University of Bordeaux
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
P. Styring, A. Quadrelli and K. Armstrong, Carbon Dioxide Utilisation, 1st edn. Closing the Carbon Cycle, Elsevier, 2015
C. Maeda Y. Miyazaki T. Ema Catal. Sci. Technol. 2014 4 1482
M. North R. Pasquale C. Young Green Chem. 2010 12 1514 1539
P. P. Pescarmona M. Taherimehr Catal. Sci. Technol. 2012 2 2169 2187
Q. He J. W. O'Brien K. A. Kitselman L. E. Tompkins G. C. T. Curtis F. M. Kerton Catal. Sci. Technol. 2014 4 1513 1528
B.-H. Xu J.-Q. Wang J. Sun Y. Huang J.-P. Zhang X.-P. Zhang S.-J. Zhang Green Chem. 2015 17 108 122
G. Fiorani W. Guo A. W. Kleij Green Chem. 2015 17 1375 1389
M. North C. Young Catal. Sci. Technol. 2011 1 93 99
P. Ramidi P. Munshi Y. Gartia S. Pulla A. S. Biris A. Paul A. Ghosh Chem. Phys. Lett. 2011 512 273 277
N. Kihara N. Hara T. Endo J. Org. Chem. 1993 58 6198 6202
T. Werner H. Büttner ChemSusChem 2014 7 3268 3271
B. Chatelet L. Joucla J. P. Dutasta A. Martinez K. C. Szeto V. Dufaud J. Am. Chem. Soc. 2013 135 5348 5351
J. Sun S.-I. Fujita M. Arai J. Organomet. Chem. 2005 690 3490 3497
L. Han M. S. Park S. J. Choi Y. J. Kim S. M. Lee D. W. Park Catal. Lett. 2011 1 8
S. Zhang Y. Huang H. Jing W. Yao P. Yan Green Chem. 2009 11 935 938
T. Seki J. D. Grunwaldt A. Baiker J. Phys. Chem. B 2009 113 114 122
J. Li L. Wang F. Shi S. Liu Y. He L. Lu X. Ma Y. Deng Catal. Lett. 2011 141 339 346
S. Udayakumar S. W. Park D. W. Park B. S. Choi Catal. Commun. 2008 9 1563 1570
Z. Z. Yang L. N. He C. X. Miao S. Chanfreau Adv. Synth. Catal. 2010 352 2233 2240
H. Y. Ju M. D. Manju K. H. Kim S. W. Park D. W. Park J. Ind. Eng. Chem. 2008 14 157 160
B. Ochiai T. Endo J. Polym. Sci., Part A: Polym. Chem. 2007 45 5673 5678
S. Foltran J. Alsarraf F. Robert Y. Landais E. Cloutet H. Cramail T. Tassaing Catal. Sci. Technol. 2013 3 1046 1055
W.-L. Wong L. Y. S. Lee K.-P. Ho Z.-Y. Zhou T. Fan Z. Lin K.-Y. Wong Appl. Catal., A 2014 472 160 166
D. Wei-Li J. Bi L. Sheng-Lian L. Xu-Biao T. Xin-Man A. Chak-Tong Catal. Today 2014 233 92 99
J. Sun S. Zhang W. Cheng J. Ren Tetrahedron Lett. 2008 49 3588 3591
L. Han H. J. Choi S. J. Choi B. Liu D. W. Park Green Chem. 2011 13 1023 1028
W. L. Dai J. Bi S. L. Luo X. B. Luo X. M. Tu C. T. Au Catal. Sci. Technol. 2014 4 556 562
O. Coulembier S. Moins V. Lemaur R. Lazzaroni P. Dubois J. CO2 Util. 2015 10 7 11
J. Tharun G. Mathai R. Roshan A. C. Kathalikkattil K. Bomi D.-W. Park Phys. Chem. Chem. Phys. 2013 15 9029 9033
A. Zhu T. Jiang B. Han J. Zhang Y. Xie X. Ma Green Chem. 2007 9 169 172
A. J. R. Amaral J. F. J. Coelho A. C. Serra Tetrahedron Lett. 2013 54 5518 5522
J. Łukaszczyk K. Jaszcz W. Kuran T. Listos Macromol. Rapid Commun. 2000 21 754 757
D. J. Darensbourg W.-C. Chung Macromolecules 2014 47 4943 4948
S. Kumar S. L. Jain B. Sain Catal. Lett. 2012 142 615 618
C. Martín G. Fiorani A. W. Kleij ACS Catal. 2015 5 1353 1370
J. W. Huang M. Shi J. Org. Chem. 2003 68 6705 6709
Y. M. Shen W. L. Duan M. Shi Eur. J. Org. Chem. 2004 3080 3089
C. J. Whiteoak A. Nova F. Maseras A. W. Kleij ChemSusChem 2012 5 2032 2038
T. Werner N. Tenhumberg H. Büttner ChemCatChem 2014 6 3493 3500
M. E. Wilhelm M. H. Anthofer M. Cokoja I. I. E. Markovits W. A. Herrmann F. E. Kühn ChemSusChem 2014 7 1357 1360
T. Werner N. Tenhumberg J. CO2 Util. 2014 7 39 45
W. Cheng Z. Fu J. Wang J. Sun S. Zhang Synth. Commun. 2012 42 2564 2573
L. Han H.-J. Choi S.-J. Choi B. Liu D.-W. Park Green Chem. 2011 13 1023 1028
J. Tharun G. Mathai A. C. Kathalikkattil R. Roshan J.-Y. Kwak D.-W. Park Green Chem. 2013 15 1673 1677
J. Song B. Zhang P. Zhang J. Ma J. Liu H. Fan T. Jiang B. Han Catal. Today 2012 183 130 135
S. Liang H. Liu T. Jiang J. Song G. Yang B. Han Chem. Commun. 2011 47 2131 2133
J. Sun W. Cheng Z. Yang J. Wang T. Xu J. Xin S. Zhang Green Chem. 2014 16 3071 3078
J. Sun J. Wang W. Cheng J. Zhang X. Li S. Zhang Y. She Green Chem. 2012 14 654 660
J. Tharun Y. Hwang R. Roshan S. Ahn A. C. Kathalikkattil D. W. Park Catal. Sci. Technol. 2012 2 1674 1680
Y. Zhao J. S. Tian X. H. Qi Z. N. Han Y. Y. Zhuang L. N. He J. Mol. Catal. A: Chem. 2007 271 284 289
C. Jing-Xian J. Bi D. Wei-Li D. Sen-Lin C. Liu-Ren C. Zong-Jie L. Sheng-Lian L. Xu-Biao T. Xin-Man A. Chak-Tong Appl. Catal., A 2014 484 26 32
D.-H. Lan F.-M. Yang S.-L. Luo C.-T. Au S.-F. Yin Carbon 2014 73 351 360
J.-Q. Wang K. Dong W.-G. Cheng J. Sun S.-J. Zhang Catal. Sci. Technol. 2012 2 1480 1484
S. Foltran R. Mereau T. Tassaing Catal. Sci. Technol. 2014 4 1585 1597
A. M. Hardman-Baldwin A. E. Mattson ChemSusChem 2014 7 3275 3278
S. Gennen M. Alves R. Méreau T. Tassaing B. Gilbert C. Detrembleur C. Jerome B. Grignard ChemSusChem 2015 8 1845 1849
S. Foltran E. Cloutet H. Cramail T. Tassaing J. Supercrit. Fluids 2012 63 52 58
B. Xiao J. Sun J. Wang C. Liu W. Cheng Synth. Commun. 2013 43 2985 2997
D. Vuluga J. Legros B. Crousse A. M. Z. Slawin C. Laurence P. Nicolet D. Bonnet-Delpon J. Org. Chem. 2011 76 1126 1133
N. Aoyagi Y. Furusho T. Endo Tetrahedron Lett. 2013 54 7031 7034
M. Alves B. Grignard S. Gennen C. Detrembleur C. Jerome T. Tassaing RSC Adv. 2015 5 53629 53636
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.