Citation: Wang Xian-Long, Li Hong-Jie, Yan Jie. Iodine-mediated regioselective hydroxyselenenylation of alkenes: Facile access to β-hydroxy selenides[J]. Chinese Chemical Letters, ;2018, 29(3): 479-481. doi: 10.1016/j.cclet.2017.06.023 shu

Iodine-mediated regioselective hydroxyselenenylation of alkenes: Facile access to β-hydroxy selenides

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310015, China

Corresponding author: Yan Jie, jieyan87@zjut.edu.cn
Received Date: 2 May 2017
Revised Date: 28 May 2017
Accepted Date: 23 June 2017
Available Online: 27 March 2017

Figures(1)

In the presence of molecular iodine, the reaction of alkenes with diselenides proceeds efficiently under air and at room temperature in mixed solvent MeCN/H₂O, which affording β-hydroxy selenides with high regioselectivity and in good to excellent yields. This iodine-mediated vicinal difunctionalization of alkenes requires mild reaction conditions and is a simple procedure, which extends the synthetic application of molecular iodine in organic synthesis.
- β-Hydroxy selenide,
- Hydroxyselenenylation,
- Diselenide,
- Alkene,
- I₂
1. [1]
  R.M. Romero, T.H. Woste, K. Muniz, Chem.-Asian J. 9(2014) 972-983. doi: 10.1002/asia.v9.4
2. [2]
  E.M. Beccalli, G. Broggini, S. Gazzola, et al., Org. Biomol. Chem. 12(2014) 6767-6789. doi: 10.1039/C4OB00610K
3. [3]
  B. Zhao, X. Peng, Y. Zhu, et al., J. Am. Chem. Soc. 133(2011) 20890-20900.
4. [4]
  H.W. Zhang, Y.C. Song, J.B. Zhao, et al., Angew. Chem., Int. Ed. 53(2014) 11079-11083. doi: 10.1002/anie.201406797
5. [5]
  C. Chen, M.B. Hecht, A. Kavara, et al., J. Am. Chem. Soc. 137(2015) 13244-13247. doi: 10.1021/jacs.5b08611
6. [6]
  K.B. Sharpless, R.F. Lauer, J. Am. Chem. Soc. 95(1973) 2697-2699. doi: 10.1021/ja00789a055
7. [7]
  H.J. Reich, F. Chow, J. Chem. Soc., Chem. Commun. 3(1975) 790-791.
8. [8]
  M. Sevring, W. Dumont, L. Hevesi, et al., Tetrahedron Lett. 17(1976) 2647-2650. doi: 10.1016/S0040-4039(00)91758-1
9. [9]
  D. Van Ende, W. Dumont, A. Krief, Angew Chem. Int. Ed. Engl. (1975) 700-702.
10. [10]
  W. Dumont, A. Krief, Angew. Chem. Int. Ed. Engl. (1975) 350-351.
11. [11]
  J.H. Rigby, U.S.M. Maharoof, M.E. Mateo, J. Am. Chem. Soc. 122(2000) 6624-6628. doi: 10.1021/ja000930i
12. [12]
  E.M. Treadwell, J.D. Neighbors, D.F. Wiemer, Org. Lett. 4(2002) 3639-3642. doi: 10.1021/ol0266368
13. [13]
  S. Knapp, D.L. Zhao, Org. Lett. 2(2000) 4037-4040. doi: 10.1021/ol0066680
14. [14]
  A. Toshimitsu, T. Aoai, H. Owada, et al., Tetrahedron 41(1985) 5301-5306. doi: 10.1016/S0040-4020(01)96781-X
15. [15]
  A. Toshimitsu, T. Aoai, H. Owada, et al., J. Chem. Soc., Chem. Commun. (1980) 412-413.
16. [16]
  M. Tingoli, R. Diana, B. Panunz, Tetrahedron Lett. 47(2006) 7529-7531. doi: 10.1016/j.tetlet.2006.08.068
17. [17]
  K.C. Nicolaou, D.A. Claremon, W.E. Barnette, et al., J. Am. Chem. Soc. 101(1979) 3704-3706. doi: 10.1021/ja00507a069
18. [18]
  M. Yoshshida, S. Sasage, K. Kawamura, et al., Bull. Chem. Soc. Jpn. 64(1991) 416-422. doi: 10.1246/bcsj.64.416
19. [19]
  M. Tiecco, L. Testaferri, A. Temperini, Synlett (2001) 1767-1771.
20. [20]
  M. Tingoli, M. Tiecco, L. Testaferri, et al., Synth. Commun. 28(1998) 1769-1778. doi: 10.1080/00397919808007007
21. [21]
  S. Torii, K. Uneyama, M. Ono, Tetrahedron Lett. 21(1980) 2741-2744. doi: 10.1016/S0040-4039(00)78594-7
22. [22]
  S.V. Ley, L.A. O'Neil, C.M.R. Low, Tetrahedron 42(1986) 5363-5368. doi: 10.1016/S0040-4020(01)82086-X
23. [23]
  M. Barahman, S. Mojgan, Synlett (2005) 1316-1318.
24. [24]
  S. Berlin, C. Ericsson, L. Engman, J. Org. Chem. 68(2003) 8386-8396. doi: 10.1021/jo030153f
25. [25]
  B. Movassagh, S. Farshbaf, Synthesis (2010) 33-35.
26. [26]
  M. Sakakibara, K. Katsumata, Y. Watanabe, et al., Synthesis (1992) 377-379.
27. [27]
  V. Ganesh, C. Srinivasan, Synthesis (2009) 3267-3278.
28. [28]
  L. Min, G. Wu, M.C. Liu, et al., J. Org. Chem 81(2016) 7584-7590. doi: 10.1021/acs.joc.6b01274
29. [29]
  R.D. Richardson, T. Wirth, Angew Chem. Int. 45(2006) 4402-4404. doi: 10.1002/(ISSN)1521-3773
30. [30]
  J. Feng, S. Liang, S.Y. Chen, et al., Adv. Synth. Catal. 354(2012) 1287-1292. doi: 10.1002/adsc.201100920
31. [31]
  K. Yang, M. Ke, Y.G. Lin, Green Chem. 17(2015) 1395-1399. doi: 10.1039/C4GC02236J
32. [32]
  Y.N. Duan, Z. Zhang, C. Zhang, Org. Lett. 18(2016) 6176-6179. doi: 10.1021/acs.orglett.6b03209
33. [33]
  S. Ambethkar, M. Vellimalai, V. Padmini, et al., New J. Chem. 41(2017) 75-80. doi: 10.1039/C6NJ02102F
34. [34]
  H.W. Shi, C. Yu, M. Zhu, et al., J. Organomet. Chem. 776(2015) 117-122. doi: 10.1016/j.jorganchem.2014.10.025
35. [35]
  H.W. Shi, C. Yu, J. Yan, Chin. Chem. Lett. 26(2015) 1117-1120. doi: 10.1016/j.cclet.2015.05.029
36. [36]
  C. Yu, H.W. Shi, M. Zhu, et al., Synlett 26(2015) 2139-2144. doi: 10.1055/s-00000083
37. [37]
  Y.K. Zhang, S.X. Wu, J. Yan, Helv Chim. Acta 99(2016) 654-658. doi: 10.1002/hlca.201600115
38. [38]
  C. Muangkaew, P. Katrun, P. Kanchanarugee, et al., Tetrahedron 69(2013) 8847-8856. doi: 10.1016/j.tet.2013.08.018
39. [39]
  Z.Z. Huang, X. Huang, Y.Z. Huang, J. Chem. Soc., Perkin Trans. I (1995) 95-96.
1. [1]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
2. [2]
  Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I₂ interface modification engineering on the performance of all-inorganic CsPbBr₃ perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
3. [3]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
4. [4]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
5. [5]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
6. [6]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
7. [7]
  Ya-Wen Zhang , Ming-Ming Gan , Li-Ying Sun , Ying-Feng Han . Supramolecular dinuclear silver(I) and gold(I) tetracarbene metallacycles and fluorescence sensing of penicillamine. Chinese Journal of Structural Chemistry, 2024, 43(9): 100356-100356. doi: 10.1016/j.cjsc.2024.100356
8. [8]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
9. [9]
  Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
10. [10]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
11. [11]
  Liang Ming , Dan Liu , Qiyue Luo , Chaochao Wei , Chen Liu , Ziling Jiang , Zhongkai Wu , Lin Li , Long Zhang , Shijie Cheng , Chuang Yu . Si-doped Li₆PS₅I with enhanced conductivity enables superior performance for all-solid-state lithium batteries. Chinese Chemical Letters, 2024, 35(10): 109387-. doi: 10.1016/j.cclet.2023.109387
12. [12]
  Xinyu Yu , Fei Wu , Xianglang Sun , Linna Zhu , Baoyu Xia , Zhong'an Li . Low-cost dopant-free fluoranthene-based branched hole transporting materials for efficient and stable n-i-p perovskite solar cells. Chinese Chemical Letters, 2024, 35(10): 109821-. doi: 10.1016/j.cclet.2024.109821
13. [13]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
14. [14]
  Renshu Huang , Jinli Chen , Xingfa Chen , Tianqi Yu , Huyi Yu , Kaien Li , Bin Li , Shibin Yin . Synergized oxygen vacancies with Mn2O3@CeO2 heterojunction as high current density catalysts for Li–O2 batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100171-100171. doi: 10.1016/j.cjsc.2023.100171
15. [15]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
16. [16]
  Maomao Liu , Guizeng Liang , Ningce Zhang , Tao Li , Lipeng Diao , Ping Lu , Xiaoliang Zhao , Daohao Li , Dongjiang Yang . Electron-rich Ni2+ in Ni3S2 boosting electrocatalytic CO2 reduction to formate and syngas. Chinese Journal of Structural Chemistry, 2024, 43(8): 100359-100359. doi: 10.1016/j.cjsc.2024.100359
17. [17]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
18. [18]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
19. [19]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
20. [20]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(540)
HTML views(8)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142