Citation: Quan Jining, He Xiaoxue, Yan Xinhuan, Li Xiaoqing, Xu Xiangsheng. Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I₂[J]. Chinese Journal of Organic Chemistry, ;2020, 40(4): 1033-1037. doi: 10.6023/cjoc201909027 shu

Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I₂

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Xu Xiangsheng, future@zjut.edu.cn
Received Date: 17 September 2019
Revised Date: 23 November 2019
Available Online: 11 December 2019
Fund Project: the Innovative Experimental Project of Zhejiang University of Technology SYXM1704the National Key Research and Development Program of China 2017YFC0210900Project supported by the National Key Research and Development Program of China (No. 2017YFC0210900) and the Innovative Experimental Project of Zhejiang University of Technology (No. SYXM1704)

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A new method for the iodocyclization of olefinic dicarbonyl compounds with t-butyl hydroperoxide (TBHP) and I₂ was developed. The in situ generated hypoiodous acid and ^tBuOI were used as active iodine cation reagents. This method allowed the synthesis of polysubstituted 5-iodomethyldihydrofurans under mild reaction conditions with cheap reagents and high atom economy.
- iodocyclization,
- olefinic dicarbonyl compounds,
- dihydrofurans,
- TBHP,
- I₂
1. [1]
  French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354. doi: 10.1039/b310389g
2. [2]
  Zhao, J.-J.; Gao, W.-C.; Chang, H.-H.; Li, X.; Liu, Q.; Wei, W.-L. Chin. J. Org. Chem. 2014, 34, 1941 (in Chinese).
3. [3]
  Lopatriello, A.; Caprioglio, D.; Minassi, A.; Moriello, A.; Formisano, C.; Petrocellis, L.; Appendino, G.; Scafati, O. Bioorg. Med. Chem. 2018, 15, 4532.
4. [4]
  Jung, M.; Ham, J.; Song, J. Org. Lett. 2002, 4, 2763. doi: 10.1021/ol026285x
5. [5]
  Rozners, E.; Liu, Y. Org. Lett. 2003, 5, 181. doi: 10.1021/ol027229z
6. [6]
  Hsu, D.-S.; Huang, J.-Y. Org. Lett. 2019, 21, 7665. doi: 10.1021/acs.orglett.9b02999
7. [7]
  Li, X.-Q.; Ding, Y.; Qian, L.-J.; Gao, Y.; Wang, X.-Q.; Yan, X.-H.; Xu, X.-S. J. Org. Chem. 2019, 84, 12656. doi: 10.1021/acs.joc.9b02031
8. [8]
  Li, X.-Q.; Wang, X.-Q.; Wang, Z.; Yan, X.-H.; Xu, X.-S. ACS Sustainable Chem. Eng. 2019, 7, 1875. doi: 10.1021/acssuschemeng.8b06096
9. [9]
  Chalker, J. M.; Thompson, A. L.; Davis, B. G. Org. Synth. 2010, 87, 288. doi: 10.15227/orgsyn.087.0288
10. [10]
  Arimistu, S.; Nakasone, M.; Gima, E. Tetrahedron Lett. 2018, 59, 887. doi: 10.1016/j.tetlet.2018.01.053
11. [11]
  Peri, F.; Bassetti, R.; Caneva, E.; Gioia, L.; Ferla, B.; Presta, M.; Tanghetti, E.; Nicotra, F. J. Chem. Soc., Perkin Trans. 1 2002, 638.
12. [12]
  Liu, J.; Liu, Q.-Y.; Fang, X.-X.; Liu, G.-Q.; Ling, Y. Org. Biomol. Chem. 2018, 16, 7454 doi: 10.1039/C8OB02161A
13. [13]
  Hu, F.; Gao, W.-C.; Chang, H.-H.; Li, X.; Wei, W.-L. Chin. J. Org. Chem. 2015, 35, 1848 (in Chinese).
14. [14]
  Kupper, F.; Feiters, M.; Olofsson, B.; Kaiho, T.; Yanagida, S.; Zimmermann, M.; Carpenter, L.; Luther, G.; Lu, Z.-L.; Jonsson, M.; Kloo, L. Angew. Chem., Int. Ed. 2011, 50, 11598. doi: 10.1002/anie.201100028
15. [15]
  Antonioletti, R.; Bonadies, F.; Scettri, A. Tetrahedron Lett. 1988, 29, 4987. doi: 10.1016/S0040-4039(00)80660-7
16. [16]
  Parvatkar, P.; Parameswaran, P.; Tilve, S. Chem.-Eur. J. 2012, 18, 5460. doi: 10.1002/chem.201100324
17. [17]
  Wan, B.-Q.; Jiang, X.-F.; Jia, G.-C.; Ma, S.-M. Eur. J. Org. Chem. 2012, 4373.
18. [18]
  Gao, X.-F.; Yang, H.-L.; Cheng, C.; Jia, Q.; Gao, F.; Chen, H.-X.; Cai, Q.; Wang, C.-J. Green Chem. 2018, 20, 2225. doi: 10.1039/C8GC00209F
19. [19]
  Li, X.-Q.; Xu, X.-S.; Shi, X.-H. Tetrahedron Lett. 2013, 54, 3071. doi: 10.1016/j.tetlet.2013.03.117
20. [20]
  Shantharjun, B.; Rajeswari, R.; Vani, D.; Unnava, R.; Sridhar, B.; Reddy, K. Asian J. Org. Chem. 2019, 8, 2162. doi: 10.1002/ajoc.201900588
21. [21]
  Li, X.-Q.; Chen, K.; Tang, Y.-C.; Zhu, H.-H.; Chen, F.; Yan, X.-H.; Xu, X.-S. Synlett 2018, 29, 1634. doi: 10.1055/s-0037-1609968
22. [22]
  Wang, H.; Chen, C.; Liu, W.-B.; Zhu, Z.-B. Beilstein J. Org. Chem. 2017, 13, 2023. doi: 10.3762/bjoc.13.200
23. [23]
  Zhu, F.-Y.; Wang, Y.-M.; He, M.-C.; Yan, Z.-H.; Lin, S. Chin. J. Org. Chem. 2019, 39, 1175 (in Chinese).
24. [24]
  Yang, N.; Yuan, G.-Q. Org. Biomol. Chem. 2019, 17, 6639. doi: 10.1039/C9OB01200A
25. [25]
  Nooy, A.; Besemer, A.; Bekkum, H. Synthesis 1996, 1153.
26. [26]
  Tang, E; Huang, X.; Xu, W.-M. Tetrahedron 2004, 60, 9963. doi: 10.1016/j.tet.2004.08.042
27. [27]
  Yang, N.-Y.; Li, Z.-L.; Ye, L.; Tan, B.; Liu, X.-Y. Chem. Commun. 2016, 52, 9052. doi: 10.1039/C6CC00364H
28. [28]
  Howard, J. L.; Sagatov, Y.; Repusseau, L.; Schotten, C.; Browne, D. L. Green Chem. 2017, 19, 2798. doi: 10.1039/C6GC03139K
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Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I2

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通讯作者: 陈斌, bchen63@163.com

Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I₂