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Synlett 2017; 28(13): 1657-1659
DOI: 10.1055/s-0036-1588794
letter
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of β-Iodonitro Alkenes via Iodonitration of Alkynes with tert-Butyl Nitrite and Iodine

Yuanyuan Fan
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
,
Bei Zhou
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
,
Kun Chen
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
,
Bingtao Wang
b   Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, P. R. China   eMail: xqli@zjut.edu.cn   eMail: future@zjut.edu.cn
,
Xiaoqing Li*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
,
Xiangsheng Xu*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
› InstitutsangabenGefördert durch: Natural Science Foundation of China (51503181)
Weitere Informationen

Publikationsverlauf

Received: 19. März 2017

Accepted after revision: 26. März 2017

Publikationsdatum:
27. April 2017 (online)

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Abstract

A convenient synthetic approach to β-iodonitro alkenes based on the iodonitration of alkynes with t BuONO and I2 is described. No acid or oxidant is required in this reaction.

Key words

β-iodonitro alkenes - iodonitration - alkynes - free radical - difunctionalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588794.
  • Supporting Information
 

  • References and Notes

    • 1a Lu Q. Zhang J. Zhao G. Qi Y. Wang H. Lei A. J. Am. Chem. Soc. 2013; 135: 11481
      CrossrefPubMed
    • 1b Yi N. Wang R. Zou H. He W. Fu W. He W. J. Org. Chem. 2015; 80: 5023
      CrossrefPubMed
    • 1c He Y.-T. Wang Q. Li L.-H. Liu X.-Y. Xu P.-F. Liang Y.-M. Org. Lett. 2015; 17: 5188
      CrossrefPubMed
    • 1d Lin Y.-M. Lu G.-P. Cai C. Yi W. Org. Lett. 2015; 17: 3310
      CrossrefPubMed
    • 1e Maji A. Hazra A. Maiti D. Org. Lett. 2014; 16: 4524
      CrossrefPubMed
    • 1f Lai J. Tian L. Huo X. Zhang Y. Xie X. Tang S. J. Org. Chem. 2015; 80: 5894
      CrossrefPubMed
    • 2a Reiser O. Angew. Chem. Int. Ed. 2006; 45: 2838
      CrossrefPubMed
    • 2b Negishi E.-I. Huang Z. Wang G. Mohan S. Wang C. Hattori H. Acc. Chem. Res. 2008; 41: 1474
      CrossrefPubMed
    • 3a Shindo M. Matsumoto K. Top. Curr. Chem. 2012; 327: 1
      PubMed
    • 3b Flynn AB. Ogilvie WW. Chem. Rev. 2007; 107: 4698
      CrossrefPubMed
  • 4 Irie M. Fukaminato T. Matsuda K. Kobatake S. Chem. Rev. 2014; 114: 12174
    CrossrefPubMed
  • 5 Tveryakova EN. Miroshnichenko YuYu. Perederina IA. Yusubov MS. Russ. J. Org. Chem. 2007; 43: 152
    Crossref
  • 6 Hlekhlai S. Samakkanad N. Sawangphon T. Pahmakotr M. Reutrakul V. Soorukram D. Jaipetch T. Kuhakarn C. Eur. J. Org. Chem. 2014; 7433
    • 7a Liu Y. Zhang J.-L. Song R.-J. Qian P.-C. Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 9017
      CrossrefPubMed
    • 7b Shen T. Yuan Y. Jiao N. Chem. Commun. 2014; 50: 554
      CrossrefPubMed
    • 7c Koley D. Colón OC. Savinov SN. Org. Lett. 2009; 11: 4172
      CrossrefPubMed
    • 7d Taniguchi T. Sugiura Y. Hatta T. Yajima A. Ishibashi H. Chem. Commun. 2013; 49: 2198
      CrossrefPubMed
    • 7e Hu M. Liu B. Ouyang X.-H. Song R.-J. Li J.-H. Adv. Synth. Catal. 2015; 357: 3332
      Crossref
    • 7f Hirose D. Taniguchi T. Beilstein J. Org. Chem. 2013; 9: 1713
      CrossrefPubMed
    • 7g Rokade BV. Prabhu KR. Org. Biomol. Chem. 2013; 11: 6713
      CrossrefPubMed
  • 8 Dutta U. Maity S. Kancherla R. Maiti D. Org. Lett. 2014; 16: 6302
    CrossrefPubMed
    • 9a Li X. Shi X. Fang M. Xu X. J. Org. Chem. 2013; 78: 9499
      CrossrefPubMed
    • 9b Li X. Xu X. Shi X. Tetrahedron Lett. 2013; 54: 3071
      Crossref
  • 10 (1-Iodo-2-nitrovinyl)benzene: Typical Procedure To a stirred solution of phenylacetylene (0.5 mmol), and I2 (0.25 mmol) in THF (2 mL) was added t BuONO (1.3 mmol) at room temperature. The mixture was stirred at 50 °C for 4 h and then cooled to room temperature. The excess solvent was removed under vacuum, and the residue was directly purified by silica gel column chromatography (petroleum/ethyl acetate = 250:1) to afford product 2a (111.3 mg, 81%, E/Z = 9:1) as a yellow oil. 1H NMR (500 MHz, CDCl3): δ = 7.73 (s, 1 H), 7.41–7.35 (m, 3 H), 7.33–7.28 (m, 2 H). 13C NMR (125 MHz, CDCl3): δ = 142.93, 138.47, 130.22, 128.55, 127.27, 113.82.
  • 11 Rusch F. Unkel L.-N. Alpers D. Hoffmann F. Brasholz M. Chem. Eur. J. 2015; 21: 8336
    CrossrefPubMed
  • 12 Mikova AV. Lipina ES. Kretser TY. Russ. J. Org. Chem. 2009; 45: 229
    Crossref
  • 13 Aleksiev D. Ivanova S. Valeva R. J. Sulfur Chem. 2008; 29: 19
    Crossref
  • 14 Volynskii VE. Perekalin VV. Sopova AS. Zh. Org. Khim. 1967; 3: 1345