Abstract
Herein, we report a chemoselective insertion of CO2 into unsaturated alkyne substrates under ambient conditions, which is achieved over poly (sulfobetain methacrylate) (p(SBMA)) supported Cu2O nanocatalyst (Cu2O/p(SBMA)) and a series of 3a,4-dihydronaphtho[2,3-c]furan-1(3H)-ones, can be obtained in excellent yields. Cu2O/p(SBMA) presents high performance for environment pressure activation and interpolation of CO2 into unsaturated alkyne substrates. This provides an attainable and competent catalyst for interpolation of CO2 into aryl alkynes, and binding allylic chlorides through SN2 mechanism in order to produce efficient ester and lactone heterocycles that are supposed to have favorable utilizations. All in all, these findings signify practical methods of hybrid catalyst development for detailed alterations, including CO2 employment in a green and sustainable manner.
Graphic Abstract
Similar content being viewed by others
References
He Z, Xia Y, Tang B, Jiang X, Su J (2016) Mater Lett 184:148–151
Li H, Su Z, Hu S, Yan Y (2017) Appl Catal B 207:134–142
Scuderi V, Amiard G, Boninelli S, Scalese S, Miritello M, Sberna PM, Impellizzeri G, Privitera V (2016) Mater Sci Semicond Process 42:89–93
Nielsen DU, Hu XM, Daasbjerg K, Skrydstrup T (2018) Nat Catal 1:244–254
Peter SC (2018) ACS Energy Lett 3:1557–1561
Wei J, Ge Q, Yao R, Wen Z, Fang C, Guo L, Xu H, Sun J (2017) Nat Commun 8:15174
Poliakoff M, Leitner W, Streng ES (2015) Faraday Discuss 183:9–17
Aresta M, Tommasi I (1997) Energ Convers Manag 38:S373–S378
Clark JH (2006) Green Chem 8:17–21
Clark JH (1999) Green Chem 1:1–8
Sheldon RA (2007) Green Chem 9:1273–1283
Sheldon RA (2016) Green Chem 18:3180–3183
Huang K, Sun CL, Shi ZJ (2011) Chem Soc Rev 40:2435–2452
Pinaka A, Vougioukalakis GC (2015) Coord Chem Rev 288:69–97
Yu D, Teong SP, Zhang Y (2015) Chem Rev 293–294:279–291
Goeppert A, Czaun M, Jones JP (2014) Chem Soc Rev 43:7995–8048
Peppel W (1958) J Ind Eng Chem 50:767–770
Shaikh AAG, Sivaram S (1996) Chem Rev 96:951–976
North M, Pasquale R (2009) Angew. Chem Int Ed 48:2946–2948
Yan P, Jing HW (2009) Adv Synth Catal 351:1325–1332
Baba A, Nozaki T, Matsuda H (1987) Bull Chem Soc Jpn 60:1552–1554
North M, Young C (2011) Catal Sci Technol 1:93–99
Supasitmongkol S, Styring P (2014) Catal Sci Technol 4:1622–1630
Elmas S, Subhani MA, Harrer M, Leitner W, Sundermeyer J, Mueller TE (2014) Catal Sci Technol 4:1652–1657
Pena Carrodeguas L, Gonzalez-Fabra J, Castro-Gomez F, Bo C (2015) Chem Eur J 21:6115–6122
Montoya CA, Paninho AB, Felix PM, Zakrzewska ME, Vital J, Najdanovic-Visak V, Nunes AVM (2015) J Supercrit Fluid 100:155–159
Macherla VR, Liu J, Sunga M, White DJ, Grodberg J, Teisan S, Lam KS, Potts BC (2007) J Nat Prod 70:1454–1457
Katayama S, Myoga A, Akahori Y (1992) J Phys Chem 96:4698–4701
Zhao Y, Chen W, Yang Y, Yang X, Xu H (2007) Colloid Polym Sci 285:1395–1400
Mohan YM, Geckeler KE (2007) React Funct Polym 67:144–155
Das M, Kumacheva E (2006) Colloid Polym Sci 284:1073–1084
Georgiev GS, Kamenska EB, Vassileva ED, Kamenova IP, Georgieva VT, Iliev SB, Ivanov IA (2006) Biomacromol 7:1329–1334
Kamenova I, Harrass M, Lehmann B, Friedrich K, Ivanov I, Georgiev G (2007) Macromol Symp 254:122–127
Das M, Sanson N, Kumacheva E (2008) Chem Mater 20:7157–7163
Chen SF, Zheng J, Li LY, Jiang SY (2005) J Am Chem Soc 127:14473–14478
Vogler EA (1998) Adv Colloid Interface Sci 74:69–117
Ratner BD, Hoffman AS, Schoen FJ, Lemons JE (2004) Biomaterials science: anintroduction to materials in medicine. Academic Press, San Diego, pp 59–65
Shih YJ, Chang Y (2010) Langmuir 26:17286–17294
Zhang Z, Chen SF, Chang Y, Jiang SY (2006) J Phys Chem B 110:10799–10804
Zhang Z, Chao T, Chen SF, Jiang SY (2006) Langmuir 22:10072–10077
Ladd J, Zhang Z, Chen SF, Hower JC, Jiang SY (2008) Biomacromol 9:1357–1361
Cheng G, Zhang Z, Chen SF, Bryers JD, Jiang SY (2007) Biomaterials 28:4192–4199
Zhang Z, Zhang M, Chen SF, Horbett TA, Ratner BD, Jiang SY (2008) Biomaterials 29:4285–4291
Zhang Z, Chao T, Liu LY, Cheng G, Ratner BD, Jiang SY (2009) J Biomat Sci Polym E 20:1845–1859
Chang Y, Chen SF, Zhang Z, Jiang SY (2006) Langmuir 22:2222–2226
Tian M, Wang J, Zhang E, Li J, Duan C, Yao F (2013) Langmuir 29:8076–8085
Heath DE, Cooper SL (2012) Acta Biomater 8:2899–2910
Zhang J, Xu S, Kumacheva E (2004) J Am Chem Soc 126:7908–7914
Ajmal M, Siddiq M, Al-Lohedan H, Sahiner N (2014) RSC Adv 4:59562–59570
Gulati U, Rajesh UC, Rawat DS, Zaleski JM (2020) Green Chem 22:3170–3177
Acknowledgement
This work was supported by the Special Scientific Research Project of Shaanxi Education Department (Nos:19JK0904, 18JK1194) and Science Research Foundation of Xijing University (Nos: XJ18T03, XJ18B05).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Zhu, Y., Xu, G., Song, W. et al. Cu2O Nanocatalysts Immobilized on p(SBMA) for Synergistic CO2 Activation to Afford Esters and Heterocycles at Ambient Pressure. Catal Lett 151, 2724–2733 (2021). https://doi.org/10.1007/s10562-020-03518-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-020-03518-z