Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO2 and Aziridine Under Atmospheric Pressure

doi:10.1007/s40242-024-3253-z

高等学校化学研究 ›› 2024, Vol. 40 ›› Issue (6): 1041-1049.doi: 10.1007/s40242-024-3253-z

Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure

LI Bohan, GONG Yujie, LOU Huimin, WEI Yujuan, GUO Liping, WANG Hongmei, ZHANG Zulei, LI Lei

Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, P. R. China

收稿日期:2023-12-20 出版日期:2024-12-01 发布日期:2024-10-26
通讯作者: GUO Liping,guolp@mail.zjxu.edu.cn;LI Lei,lei.li@mail.zjxu.edu.cn E-mail:guolp@mail.zjxu.edu.cn;lei.li@mail.zjxu.edu.cn
基金资助:
This work was supported by the Program for Public Technology of Jiaxing Province, China (No. 2023AD11041), the Natural Science Foundation of Zhejiang Province, China (No. LY22E020009), the National Undergraduate Training Programs for Innovation of China (No. 202110354038) and the Student Research Training Program of Jiaxing University, China (No. 8517231462).

Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure

LI Bohan, GONG Yujie, LOU Huimin, WEI Yujuan, GUO Liping, WANG Hongmei, ZHANG Zulei, LI Lei

Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, P. R. China

Received:2023-12-20 Online:2024-12-01 Published:2024-10-26
Contact: GUO Liping,guolp@mail.zjxu.edu.cn;LI Lei,lei.li@mail.zjxu.edu.cn E-mail:guolp@mail.zjxu.edu.cn;lei.li@mail.zjxu.edu.cn
Supported by:
This work was supported by the Program for Public Technology of Jiaxing Province, China (No. 2023AD11041), the Natural Science Foundation of Zhejiang Province, China (No. LY22E020009), the National Undergraduate Training Programs for Innovation of China (No. 202110354038) and the Student Research Training Program of Jiaxing University, China (No. 8517231462).

摘要/Abstract

摘要： Metal acetylacetonates, a type of readily synthesized or commercially available metal complex, were demonstrated to be robust catalysts for the synthesis of oxazolidinone from CO₂ and aziridine under condition of atmospheric pressure and mild temperature, exhibiting high chemo- and regio-selectivity. Tetrabutylammonium halides were employed as cocatalysts in the reaction, and it was believed that the reaction activity was influenced by a balance of anions’ two abilities, namely their nucleophilicity in ring-opening of aziridines and their leaving capacity in ring-closing of intermediate carbamate salts to form oxazolidinones. Notably, higher nucleophilicity of these anions resulted in increased formation of dimers, which served as by-products of the reaction. The study of mechanism suggested that there should be an alternative pathway involving CO₂ derivative acting as a nucleophile during the ring-opening process, and this pathway could not be ignored when conventional nucleophiles, such as tetrabutylammonium halides are absent.

关键词: Metal acetylacetonate, Carbon dioxide, Aziridine, Oxazolidinone, Atmospheric pressure

Abstract: Metal acetylacetonates, a type of readily synthesized or commercially available metal complex, were demonstrated to be robust catalysts for the synthesis of oxazolidinone from CO₂ and aziridine under condition of atmospheric pressure and mild temperature, exhibiting high chemo- and regio-selectivity. Tetrabutylammonium halides were employed as cocatalysts in the reaction, and it was believed that the reaction activity was influenced by a balance of anions’ two abilities, namely their nucleophilicity in ring-opening of aziridines and their leaving capacity in ring-closing of intermediate carbamate salts to form oxazolidinones. Notably, higher nucleophilicity of these anions resulted in increased formation of dimers, which served as by-products of the reaction. The study of mechanism suggested that there should be an alternative pathway involving CO₂ derivative acting as a nucleophile during the ring-opening process, and this pathway could not be ignored when conventional nucleophiles, such as tetrabutylammonium halides are absent.

Key words: Metal acetylacetonate, Carbon dioxide, Aziridine, Oxazolidinone, Atmospheric pressure

LI Bohan, GONG Yujie, LOU Huimin, WEI Yujuan, GUO Liping, WANG Hongmei, ZHANG Zulei, LI Lei. Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure[J]. 高等学校化学研究, 2024, 40(6): 1041-1049.

参考文献

[1] Lindsey R., Climate Change: Atmospheric Carbon Dioxide, https:// www.climate.gov/news-features/understanding-climate/climate-change-atmospheric-carbon-dioxide (accessed 25/07/2023).
[2] Global Monitoring Laboratory, Trends in Atmospheric Carbon Dioxide, https://www.esrl.noaa.gov/gmd/ccgg/trends (accessed 25/07/2023).
[3] Zahasky C., Krevor S., Energ. Environ. Sci., 2020, 13, 1561
[4] Burkart M., Hazari D. N., Tway C. L., Zeitler E. L., Acs Catal., 2019, 9, 7937.
[5] Wang L., Qi C. R., Xiong W. F., Jiang H. F., Chin. J. Catal., 2022, 43, 1598.
[6] Zhang Z., Deng Y., Zhang Q. F., Yu D. G., Chem. J. Chinese Universities, 2022, 43, 20220255.
[7] Zhou C., Li M., Yu J. T., Sun S., Cheng J., Chin. J. Org. Chem., 2020, 40, 2221.
[8] Ran C. K., Xiao H. Z., Liao L. L., Ju T., Zhang W., Yu D. G., Natl. Sci. Open, 2023, 2, 20220024.
[9] Foti C., Piperno A., Scala A., Giuffre O., Molecules, 2021, 26, 4280.
[10] Pons A., Delion L., Poisson T., Charette A. B., Jubault P., Acc. Chem. Res., 2021, 54, 2969.
[11] Cannizzaro C. E., Ashley J. A., Janda K. D., Houk K. N., J. Am. Chem. Soc., 2003, 125, 2489.
[12] Fournier A. H., Robillard G., Devillers C. H., Plasseraud L., Andrieu J., Eur. J. Org. Chem., 2016, 21, 3514.
[13] Zhu H. T., Chen P. H., Liu G. S., J. Am. Chem. Soc., 2014, 136, 1766.
[14] Liu X. F., Wang M. Y., He L. N., Curr. Org. Chem., 2017, 21, 698.
[15] Ye J. H., Ju T., Huang H., Liao L. L., Yu D. G., Acc. Chem. Res., 2021, 54, 2518.
[16] Ye J. H., Song L., Zhou W. J., Ju T., Yin Z. B., Yan S. S., Zhang Z., Li J., Yu D. G., Angew. Chem. Int. Ed., 2016, 55, 10022.
[17] Zhang Z., Ye J. H., Wu D. S., Zhou Y. Q., Yu D. G., Chem. Asian J., 2018, 13, 2292.
[18] Zhu X. Y., Ran C. K., Wen M., Guo G. L., Liu Y., Liao L. L., Li Y. Z., Li M. L., Yu D. G., Chin. J. Chem., 2021, 39, 3231.
[19] Arshadi S., Banaei A., Ebrahimiasl S., Monfared A., Vessally E., RSC Adv., 2019, 9, 19465.
[20] Chen Y. J., Ren Q. G., Zeng X. J., Tao L. M., Zhou X. T., Ji H. B., Chem. Eng. Sci., 2021, 232, 116380.
[21] Chen Y. J., Luo R. C., Yang Z., Zhou X. T., Ji H. B., Sustain. Energ. Fuels, 2018, 2, 125.
[22] Sengoden M., North M., Whitwood A. C., Chemsuschem., 2019, 12, 3296.
[23] Adhikari D., Miller A. W., Baik M.-H., Nguyen S. T., Chem. Sci., 2015, 6, 1293.
[24] Xie Y., Lu C., Zhao B., Wang Q., Yao Y., J. Org. Chem., 2019, 84, 1951.
[25] Bresciani G., Zacchini S., Marchetti F., Pampaloni G., Dalton Trans., 2021, 50, 5351.
[26] Wang T., Mu Z., Ding X., Han B., Chem. Res. Chinese Universities, 2022, 38, 446.
[27] Bresciani G., Bortoluzzi M., Pampaloni G., Marchetti F., Org. Bio. Chem., 2021, 19, 4152.
[28] Zhao Y. N., Yang Z. Z., Luo S. H., He L. N., Catal. Today., 2013, 200, 2.
[29] Yang Z. Z., He L. N., Peng S. Y., Liu A. H., Green Chem., 2010, 12, 1850.
[30] Damiano C., Sonzini P., Manca G., Gallo E., Eur. J. Org. Chem., 2021, 19,2807.
[31] Sonzini P., Damiano C., Intrieri D., Manca G., Gallo E., Adv. Synth. Catal., 2020, 362, 2961.
[32] Ueno A., Kayaki Y., Ikariya T., Green Chem., 2013, 15, 425.
[33] Liu A. H., Dang Y. L., Zhou H., Zhang J. J., Lu X. B., Chemcatchem., 2018, 10, 2686.
[34] Du Y., Wu Y., Liu A. H., He L. N., J. Org. Chem., 2008, 73, 4709.
[35] Helal A., Fettouhi M., Arafat M. E., Khan M. Y., Sanhoob M. A., J. CO₂ Util., 2021, 50, 101603.
[36] Liu A. G., Chen Y., Liu P. D., Qi W., Li B., Inorg. Chem. Front., 2022, 9, 4425.
[37] Wang X., Gao W. Y., Niu Z., Wojtas L., Perman J. A., Chen Y. S., Li Z., Aguila B., Ma S. Q., Chem. Commun., 2018, 54, 1170.
[38] Shi Y., Zhao J., Xu H., Hou S.L., Zhao B., Sci. China Chem., 2021, 64, 1316.
[39] Aresta M., Dibenedetto A., Angelini A., Chem. Rev., 2014, 114, 1709.
[40] Vigato R. A., Peruzzo V., Tamburini S., Coord. Chem. Rev., 2009, 253, 1099.
[41] Yang Z. Z., Li Y. N., Wei Y. Y., He L. N., Green Chem., 2011, 13, 2351.
[42] Wang H. M., Zhang Z. L., Wang H. L., Guo L. P., Li L., Dalton Trans., 2019, 48, 15970.
[43] Kumar S., Jain S. L., Sain B., Catal. Lett., 2012, 142, 615.
[44] Guo L. P., Lamb K. J., North M., Green Chem., 2021, 23, 77.
[45] Phung C., Ulrich R. M., Ibrahim M., Tighe N. T. G., Lieberman D. L., Pinhas A. R., Green Chem., 2011, 13, 3224.
[46] Phung C., Tantillo D. J., Hein J. E., Pinhas A. R., J. Phys. Org. Chem., 2018, 31, e3735.
[47] Dou X. Y., He L. N., Yang Z. Z., Wang J. L., Synlett., 2010, 14, 2159.

Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure

Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure

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