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DOI: https://doi.org/10.6023/cjoc202602005

ARTICLE

Direct synthesis of β-hydroxyesters via cobalt-catalyzed carbonylation of epoxides

  • De-Yang Liu ,
  • Tao Zhou ,
  • Bing-Feng Shi
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  • State Key Laboratory of Soil Pollution Control and Safety, Department of Chemistry, Zhejiang University, Hangzhou 310058, China.

Received date: 2026-02-03

  Revised date: 2026-03-23

  Online published: 2026-04-21

Supported by

National Natural Science Foundation of China (22525011, U25A20547, U22A20388, 92256302 for Bing-Feng Shi, 22271250 for Tao Zhou), and Fundamental and Interdisciplinary Disciplines Breakthrough Plan of the Ministry of Education of China (JYB2025XDXM407).

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Abstract

β-Hydroxyesters are important skeletons in numerous bioactive compounds, pharmaceuticals, and natural products. We report here a highly efficient and straightforward method for synthesizing β-hydroxy esters via cobalt-catalyzed carbonylation of epoxides with carbon monoxide using tri(pyridin-2-yl)phosphane as the ligand. Both monosubstituted and disubstituted epoxides are well tolerated in the reaction.

Key words： cobalt-catalyzed; epoxides; carbonylation; β-hydroxyesters

Cite this article

De-Yang Liu , Tao Zhou , Bing-Feng Shi . Direct synthesis of β-hydroxyesters via cobalt-catalyzed carbonylation of epoxides[J]. Chinese Journal of Organic Chemistry, 0 : 6 -6 . DOI: 10.6023/cjoc202602005

References

[1] Jao, C.-W.; Lin, W.-C.; Wu, Y.-T.; Wu, P.-L. J. Nat. Prod. 2008, 71, 1275.
[2] Li, Y.-Z.; Peng, D.-Y.; Dai, M.; Xiao, C.-M.; Jiang, H.-B.; Huang, J. Nat. Prod. Res. 2012, 27, 837.
[3] Alarcón, B.; González, M. E.; Carrasco, L. Antimicrob. Agents Chemother. 1984, 26, 702.
[4] Park, J.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2018, 57, 16152.
[5] Ju, X.; Beaudry, C. M. Angew. Chem., Int. Ed. 2019, 58, 6752.
[6] (a) Reger, M. A.; Henderson, S. T.; Hale, C.; Cholerton, B.; Baker, L. D.; Watson, G. S.; Hyde, K.; Chapman, D.; Craft, S. Neurobiol. Aging 2004, 25, 311.
(b) Zhang, J.-Y.; Cao, Q.; Li, S.-W.; Lu, X.-Y.; Zhao, Y.-X.; Guan, J.-S.; Chen, J.-C.; Wu, Q.; Chen, G.-Q. Biomaterials 2013, 34, 7552.
[7] Tieu, K.; Perier, C.; Caspersen, C.; Teismann, P.; Wu, D.-C.; Yan, S.-D.; Naini, A.; Vila, M.; Jackson-Lewis, V.; Ramasamy, R.; Przedborski, S. J Clin Invest. 2003, 112, 892.
[8] (a) Sudesh, K.; Abe, H.; Doi, Y. Prog. Polym. Sci. 2000, 25, 1503.
(b) Slater, S. C.; Gerngross, T. U. Sci. Am. 2000, 283, 36.
[9] Zong, X.-L.; Liu, S.-L.; Zhang, Z.-G.; Ji, L.; Zhang, T.; Jia, Z.-H.; Loh, T.-P. J. Org. Chem. 2022, 87, 6918.
[10] (a) Lv, Y.-F.; Liu, G.; Shi, Z.-X.; Wang, Z.-B.; Angew. Chem. Int. Ed. 2024, 63, e202406109.
(b) Cozzi, P. G. Angew. Chem. Int. Ed. 2006, 45, 2951.
(c) Fernández-Ibáñez, M. Á.; Maciá, B.; Minnaard, A. J.; Feringa, B. L. Angew. Chem. Int. Ed. 2008, 120, 1337.
[11] (a) Green, T. K.; Damarancha, A.; Vanagel, M.; Showalter, B.; Kolberg, S.; Thompson, A. Eur. J. Org. Chem. 2019, 4080.
(b) Zheng, L.-S.; Férard, C.; Phansavath, P.; Ratovelomanana-Vidal, V. Chem. Commun., 2018, 54, 283.
(c) Tartaggia, S.; Fogal, S.; Motterle, R.; Ferrari, C.; Pontini, M.; Aureli, R.; Lucchi, O. D. Eur. J. Org. Chem. 2016, 3162.
[12] Wang, Y.-W.; Tang, S.-Y.; Yang, G.-Q.; Wang, S.-Y.; Ma, D.-K.; Qiu, Y.-A. Angew. Chem. Int. Ed. 2022, 61, e202207746.
[13] (a) Su, L.; Yang, X.; Yan, J.; Jiang, Y.-L.; Chen, L.-J.; Zheng, Q.-S.; Liu, J.-W. Chin. J. Org. Chem. 2025, 45, 2007 (in Chinese).
(苏雷, 杨熙, 闫捷, 蒋元力, 陈丽娟, 郑庆舒, 刘家旺, 有机化学, 2025, 45, 2007.)
(b) Wang, Y.-W.; Wang, P.; Shi, H.-B.; Zhang, C.-F.; Zhao, D.-M.; Yang, G.-A.; Yan, Y.-Z.; Feng, B.-L. Chin. J. Org. Chem. 2025, 45, 104 (in Chinese).
(王耀伟, 王鹏, 史会兵, 张成富, 赵德明, 杨桂爱, 晏耀宗, 冯保林, 有机化学, 2025, 45, 104.)
(c) Shi, H.-B.; Wang, Y.-W.; Wang, P.; Zhao, D.-M.; Feng, B.-L.; Yan, Y.-Z.; Yang, G.-A. Chin. J. Org. Chem. 2024, 44, 1811 (in Chinese).
(史会兵, 王耀伟, 王鹏, 赵德明, 冯保林, 晏耀宗, 杨桂爱, 有机化学, 2024, 44, 1811.)
(d) Li, L.-J.; He, Y.-L.; Yang, Y.-H.; Guo, J.; Lu, Z.; Wang, C.-Y.; Zhu, S.-L.; Zhu, S.-F. CCS Chem. 2024, 6, 537.
(e) Zhang, Y.-T.; Zhao, N.; Lv, B.-L.; Chen, Y.-F. Green Synth. Catal. DOI: 10.1016/j.gresc.2025.12.009.
[14] (a) Wang, C.; Luo, L.; Yamamoto, H. Acc. Chem. Res. 2016, 49, 193.
(b) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev., 2011, 40, 4986.
(c) Peng, J.-B.; Wu, F.-P.; Wu, X.-F. Chem. Rev. 2019, 119, 2090.
[15] Eisenmann, J. L.; Yamartino, R. L.; Howard Jr, J. F. J. Org. Chem. 1961, 26, 2102.
[16] Heck, R. F. J. Am. Chem. Soc. 1963, 85, 1460.
[17] Denmark, S. E.; Ahmad, M. J. Org. Chem. 2007, 72, 9630.
[18] Xu, J.-X.; Wu, X.-F. J. Org. Chem. 2019, 84, 9907.
[19] (a) Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164.
(b) Goodman, S. N.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, 4703.
[20] Deng, F.-G.; Hu, B.; Sun, W.; Chen, J.; Xia, C.-G. Dalton Trans., 2007, 4262.
[21] (a) Guo, Z.-M.; Wang, H.-S.; Lv, Z.-G.; Wang, Z.-H.; Nie, T.; Zhang, W.-W. J. Organomet. Chem. 2011, 696, 3668.
(b)Zhao, J.-B.; Wu, P.; Lai, E.-Y.; Li, J.-C.; Chen, Y.-L.; Jiang, W.-J.; Wang, B.-J.; Zhu, H.-P. Chem Asian J. 2021, 16, 3453.
(c) Liu, J.-H.; Wu, H. Xu, L.-W.; Chen, J.; Xia, C.-G. J. Mol. Catal. A:Chem. 2007, 269, 97.
(d) Zhang, W.; Han, F.; Tong, J.; Xia, C.-G.; Liu, J.-H. Chin. J. Catal 2017, 38, 805.
(e) Rajendiran, S.; Gunasekar, G. H.; Yoon, S. New J. Chem. 2018, 42, 12256.
(f) Hamasaki, A.; Muto, A.; Haraguchi, S.; Liu, X.-H.; Sakakibara, T.; Yokoyama, T.; Tokunaga, M. Tetrahedron Lett. 2011, 52, 6869.
(g) Zeng, B.; Chen, L.; Zhu, G.-L.; Yang, B.-X.; Xia, C.-G.; He, L. Mol. Catal. 2020, 494, 111109.
[22] (a) Ruwizhi, N.; Maseko, R. B.; Aderibigbe, B. A. Pharmaceutics 2022, 14, 504.
(b) Kim, J.-Y.; Shin, H.-I.; Lee, S.-E.; Piao, H.-Y.; Rejinold, N. S.; Choi, G.; Choy, J.-H. Biomater. Sci. 2022, 10, 5980.
(c) Efferth, T. Biochem. Pharmacol. 2017, 139, 107.
[23] Fachinetti, G.; Fochi, G.; Funaioli, T. J. Organomet. Chem. 1986, 301, 91.
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