研究论文

锆路易斯酸催化的环状β-二羰基化合物的de Mayo型扩环反应

  • 王钧锋 ,
  • 刘芮碹 ,
  • 米学玲 ,
  • 罗三中
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  • a北京师范大学,化学学院 北京 100875;
    b清华大学,化学系,基础分子科学中心 北京 100084

收稿日期: 2026-07-15

  修回日期: 2026-07-31

  网络出版日期: 2026-08-24

基金资助

国家自然科学基金(22393891)及国家重点研发计划(2023YFA1506401 and 2023YFA1506402)资助项目.

Zirconium Lewis Acid-Catalyzed de Mayo-Type Ring Expansion of Cyclic β-Dicarbonyls

  • Junfeng Wang ,
  • Ruixuan Liu ,
  • Xueling Mi ,
  • Sanzhong Luo
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  • aCollege of Chemistry, Beijing Normal University, Beijing, 100875;
    bCenter of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, 100084

Received date: 2026-07-15

  Revised date: 2026-07-31

  Online published: 2026-08-24

Supported by

Natural Science Foundation of China (22393891), the National Key R&D Program of China (2023YFA1506401 and 2023YFA1506402).

摘要

本文报道了锆路易斯酸催化的de Mayo型扩环反应。反应仅使用低价易得的氯化锆作为催化剂,无需使用任何外部光敏剂和添加剂。反应通过环状β-二羰基化合物与烯烃之间的自由基环加成和逆羟醛串联过程进行,不仅可在室温条件下高效进行,且具有良好的底物适用性。该策略旨在通过易得的起始原料,合成一系列官能团化的中环骨架。

本文引用格式

王钧锋 , 刘芮碹 , 米学玲 , 罗三中 . 锆路易斯酸催化的环状β-二羰基化合物的de Mayo型扩环反应[J]. 有机化学, 0 : 202607015 . DOI: 10.6023/cjoc202607015

Abstract

Zirconium-Lewis acid was developed to facilitate a de Mayo-type ring expansion reaction in the absence of external photosensitizers and additives. The reaction proceeds through a [2+2] cycloaddition and retro-Aldol sequence between cyclic β-ketocarbonyls and alkenes, which are compatible with various substrates in good yields. Through this strategy, a series of functionalized medium sized-ring skeletons can be constructed starting from readily available starting materials.

参考文献

[1] Yu X.; Zhang C.; Wang L.; Li J.; Li T.; Wei, W. Org. Chem. Front.2022, 9, 4757.
[2] Chen L.; Huang, H. ; Luo, B.; Liu J.; Yang S.; Fang, X. New J. Chem.2022, 47, 41.
[3] Vitaku E.; Smith D. T.; Njardarson, J. T. J. Med. Chem.2014, 57, 10257.
[4] Trost B. M.; Zuo Z.; Schultz, J. E. Chem. Eur. J.2020, 26, 15354.
[5] Chen P.; Liang L.; Zhu Y.; Xing Z.; Jia Z.; Loh, T. Chin. Chem. Lett.2024, 35, 109229.
[6] Paulisch T.; Mai L.; Kalthoff F.; James M. J.; Henkel C.; Guldi D. M.; Glorius, F. Angew. Chem. Int. Ed.2022, 61, e202112695.
[7] Xing Z.; Fang B.; Luo S.; Xie X.; Wang X. Org. Lett.2022, 24, 4034.
[8] Hu Y.; Li L.; Han J.; Min L.; Li C. Chem. Rev.2020, 120, 5910.
[9] Clarke A. K.; Unsworth, W. P. Chem. Sci.2020, 11, 2876.
[10] De Mayo P.; Takeshi, H. Can. J. Chem.1963, 41, 440-449.
[11] Salaverri N.; Alemán J.; Marzo, L. Adv. Synth. Catal.2024, 366, 156.
[12] Haya M.R.; Marzo L.; König B. Chem. Commun.2018, 54, 11602.
[13] Sun X.; Liu Y.; Yin Y.; Ban X.; Zhao X.; Jiang Z. Nat. Chem.2024, 16, 1169.
[14] Zhang W.; Zhang L.; Luo, S. J. Am. Chem. Soc.2023, 145, 14227.
[15] Marzo L.; Pagire S. K.; Reiser O.; König, B. Angew. Chem. Int. Ed.2018, 130, 10188.
[16] Kelch R. M.; Whyte A.; Lee E.; Yoon, T. P. Org. Lett.2023, 25, 4098.
[17] Salaverri N.; Mas-Ballesté R.; Marzo L.; Alemán J. Commun. Chem.2020, 3, 132.
[18] Lutteke G.; AlHussainy R.; Wrigstedt P. J.; Hue B.; Gelder R.; Maarseveen J. H.; Hiemstra, H. Eur. J. Org. Chem.2008, 925.
[19] Tymann D. C.; Bednarzick U.; Iovkova B. L.; Rehbein J.; Hiersemann, M. Angew. Chem. Int. Ed.2018, 130, 15779.
[20] Zhang W.; Luo S. Chem. Commun.2022, 58, 12979.
[21] Yang C.; Hu M.; Hu C.; Mi X.; Luo, S. Chem. Eur. J.2024, 30, e202402965.
[22] Norrish R. G. W.; Bamford C. H. Nature.1936, 12, 1016
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