Frustrated Ion-Pair Catalyzed Efficient Deprotection of Acetals and Ketals

  • Chao Yang ,
  • Ruoqi Li ,
  • Yu Zhang ,
  • Ming Zou ,
  • Peng Chen ,
  • Zhenhua Jia
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  • aCollege of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou, 450001;
    bDepartment of Chemistry, Fudan University, Shanghai, 200433

Received date: 2026-04-28

  Revised date: 2026-05-21

  Online published: 2026-07-06

Supported by

National Natural Science Foundation of China (No.22401080) and the Start-up Grant of Henan University of Technology (No.2023BS006).

Abstract

Acetals and ketals are among the most important protecting groups for carbonyl groups and are widely used in synthetic chemistry. In this work, we presented an efficient deprotection reaction for cyclic acetals and ketals catalyzed by triaryl carbenium ion-pair. Under mild and metal-free conditions within only 20 minutes, a wide range of carbonyl products were obtained in high yields (up to 98%) with excellent functional group tolerance, including aldehydes, ketones and natural products. Moreover, this deprotection process was practical for gram-scale synthesis, featuring simple operation and practical application.

Cite this article

Chao Yang , Ruoqi Li , Yu Zhang , Ming Zou , Peng Chen , Zhenhua Jia . Frustrated Ion-Pair Catalyzed Efficient Deprotection of Acetals and Ketals[J]. Chinese Journal of Organic Chemistry, 0 : 4046 . DOI: 10.6023/cjoc202604046

References

[1] (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons, Inc: New York, 1999.
(b) Hanson, J. R. Protecting Groups in Organic Synthesis, 1st ed.; Blackwell Science, Inc: Malden, MA, 1999.
(c) Kocienski, P. J. Protecting Groups, 1st ed.; Georg Thieme Verlag: Stuttgart, 1994.
(d) Wuts, P. G. M. Greene’s Protective Groups in Organic Synthesis, 5th edn, John Wiley & Sons Inc, 2014, pp. 554-685.
[2] (a) Torii, S.; Inokuchi, T.; Takagishi, S.; Horike, H.; Kuroda, H.; Uneyama, K. Bull. Chem. Soc. Jpn. 1987, 60, 2173-2188.
(b) Masui, M.; Kawaguchi, T.; Ozaki, S.J. Chem. Soc., Chem. Commun. 1985, 1484-1485.
(c) Martre A.-M.; Mousset G.; Rhlid R. B.; Veschambre H. Tetrahedron Lett.1990, 31, 2599-2602.
(d) Noji M.; Ishimaru S.; Obata H.; Kumaki A.; Seki T.; Hayashi, S. Takanami, T. Tetrahedron Lett.2022, 104, 154026.
[3] Gregg B. T.; Golden K. C.; Quinn, J. F. J. Org. Chem.2007, 72, 5890-5893.
[4] Olson M. E.; Carolan J. P.; Chiodo M. V.; Lazzara P. R.; Mohan, R. S. Tetrahedron Lett.2010, 51, 3969-3971.
[5] Fujioka H.; Sawama Y.; Murata N.; Okitsu T.; Kubo O.; Matsuda S.; Kita, Y. J. Am. Chem. Soc.2004, 126, 11800-11801.
[6] Fujioka H.; Okitsu T.; Sawama Y.; Murata N.; Li R.; Kita, Y. J. Am. Chem. Soc.2006, 128, 5930-5938.
[7] Yuan C.; Yang L.; Yue G.; Yu T.; Zhong W.; Liu B. Tetrahedron Lett.2012, 53, 6972-6976.
[8] Abe Y.; Yamada T.; Yamamoto T.; Esaka Y.; Ikawa T.; Sajiki H. Green Chem.2025, 27, 5464-5470.
[9] Li L.; He Z.; Zhang Z.; Jia Z.; Loh, T.-P. Chin. J. Org. Chem.2024, 44, 421-437 (in Chinese).
(李路瑶,贺忠文,张振国,贾振华,罗德平,有机化学,2024,44,421-437.)
[10] Zhang Z.; Liu X.; Ji L.; Zhang T.; Jia Z.; Loh T.-P.ACS Catal. 2022, 12, 2052-2057.
[11] Zhang Z.; Lv Y.; Ong W. Q. R.; Zhao X.; Jia Z.; Loh, T.-P. Angew. Chem. Int. Ed.2024, 63, e202408509.
[12] Zhu Y.; Yang C.; Lin Q.; Li J.; Loh T.-P.; Chen P.; Jia Z.Org. Lett. 2025, 27, 2110-2115.
[13] Wang L.; Mondal B.; Li B.; Zhang Z.; Loh T.-P.; Chen P.; Jia Z. ACS Catal.2025, 15, 19777-19785.
[14] Mondal B.; Wang L.; Wang S.; Loh T.-P. JACS Au.2026, 6, 357-366.
[15] Chen P.; Zou M.; Zhang Y.; Li N.; Li R.; Liang L.; Zhang Z.; Loh T.-P.; Jia Z. Green Chem.2026, 28, 4029-4035.
[16] (a) Totherow W. D.; Gleicher, G. J. J. Am. Chem. Soc.1969, 91, 7150-7154.
(b) Hansch C.; Leo A.; Taft, R. W. A Chem. Rev.1991, 91, 165-195.
[17] Marcantoni E.; Nobili F.; Bartoli G.; Bosco M.; Sambri, L. J. Org. Chem.1997, 62, 4183-4184.
[18] Furuta K.; Nagata T.; Yamamoto H. Tetrahedron Lett.1988, 29, 2215-2218.
[19] Tanemura K.; Suzuki T. Chem. Lett.2015, 44, 797-799.
[20] To T. A.; Nguyen, T. V. Angew. Chem. Int. Ed.2024, 63, e202317003.
[21] Barlow J. W.; McHugh A. P.; Woods O.; Walsh, J. J. Eur. J. Med. Chem.2011, 46, 1545-1554.
[22] Ma N.-N.; Hu X.-B.; Wu Y.-S.; Zheng Y.-W.; Ma M.; Chu X.-Q.; Xu H.; Luo H.; Shen Z.-L. Org. Lett.2023, 25, 1771-1775.
[23] Yan Y.; Sun S.; Cheng, J. J. Org. Chem.2017, 82, 12888-12891.
[24] Su M.; Huang X.; Lei C.; Jin J. Org. Lett.2022, 24, 354-358.
[25] Furuta K.; Nagata T.; Yamamoto H. Tetrahedron Lett.1988, 29, 2215-2218.
[26] Abe Y.; Yamada T.; Yamamoto T.; Esaka Y.; Ikawa T.; Sajiki H. Green Chem.2025, 27, 5464.
[27] Yi H.; Niu L.; Wang S.; Liu T.; Singh A. K.; Lei A. Org. Lett.2017, 19, 122-125.
[28] Jiang F.; Chen Y.; Zhang Q.; Wang W.Synlett 2024, 35, 2138-2142.
[29] Ma N.-N.; Hu X.-B.; Wu Y.-S.; Zheng Y.-W.; Ma M.; Chu X.-Q.; Xu H.; Luo H.; Shen Z.-L. Org. Lett.2023, 25, 1771-1775.
[30] Kim H.; Goseki R.; Homma C.; Ishizone T. Macromolecules2023, 56, 8796-8805.
[31] Yang T.; Liu Q.; Cheng Y.; Cai W.; Ma Y.; Yang L.; Wu Q.; Orband-Miller L. A.; Zhou L.; Xiang Z.; Huxdorf M.; Zhang W.; Zhang J.; Xiang J.-N.; Leung S.; Qiu Y.; Zhong Z.; Elliott J. D.; Lin X.; Wang, Y. ACS Med. Chem. Lett.2014, 5, 65-68.
[32] D’Hollander A. C. A.; Westwood N. J. Tetrahedron2018, 74, 224-239.
[33] Hergert T.; Varga B.; Thurner A.; Faigl F.; Mátravölgyi B.Tetrahedron 2018, 74, 2002-2008.
[34] Kang S.-H.; Lee D.; Kim H.; Choi W.; Oh J.; Oh J. H.; Yang, C. ACS Appl. Mater. Interfaces2021, 13, 52840-52849.
[35] Lindroth R.; Ondrejková A.; Wallentin C.-J. Org. Lett.2022, 24, 1662-1667.
[36] Katritzky A. R.; Odens H. H.; Voronkov, M. V. J. Org. Chem.2000, 65, 1886-1888.
[37] McKiernan G. J.; Hartley, R. C. Org. Lett.2003, 5, 4389-4392.
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