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Difluoromethylation of 2-hydroxychalcones using sodium 2-chloro-2,2-difluoroacetate as difluoromethylating agent

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Abstract

Difluoromethylation of 2-hydroxychalcones using sodium 2-chloro-2,2-difluoroacetate as the difluoromethylating agent was developed. Under facile conditions, a wide range of aryl difluoromethyl ethers were obtained in yields of 36%–80%. It is noteworthy that the new addition products, 2,2-difluoro-2H-benzofuran derivatives, were also synthesized in the reactions. The yield of 2,2-difluoro-2H-benzofuran derivative could be up to 35% when 3-methyl-2-hydroxychalcone was used as the reactant. A plausible reaction mechanism was proposed.

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References

  1. Müller K., Faeh C., Diederich F., Science, 2007, 317, 1881

    Article  Google Scholar 

  2. Purser S., Moore P. R., Swallow S., Gouverneur V., Chem. Soc. Rev., 2008, 37, 320

    Article  CAS  Google Scholar 

  3. Hagmann W. K., J. Med. Chem., 2008, 51, 4359

    Article  CAS  Google Scholar 

  4. Amatamey S. M., Honer M., Schubiger P. A., Chem. Rev., 2008, 108, 1501

    Article  Google Scholar 

  5. Ma J. A., Cahard D., Chem. Rev., 2008, 108, PR1

  6. Furuya T., Kamlet A. S., Ritter T., Nature, 2011, 473, 470

    Article  CAS  Google Scholar 

  7. Tomashenko O. A., Grushin V. V., Chem. Rev., 2011, 111, 4475

    Article  CAS  Google Scholar 

  8. Nie J., Guo H. C., Cahard D., Ma J. A., Chem. Rev., 2011, 111, 455

    Article  CAS  Google Scholar 

  9. Hollingworth C., Gouverneur V., Chem. Commun., 2012, 48, 2929

    Article  CAS  Google Scholar 

  10. Besset T., Schneider C., Cahard D., Angew. Chem. Int. Ed., 2012, 51, 5048

    Article  CAS  Google Scholar 

  11. Liang T., Neumann C. N., Ritter T., Angew. Chem. Int. Ed., 2013, 52, 8214

    Article  CAS  Google Scholar 

  12. Wang J., Sánchez-Roselló M., Aceña J. L., del Pozo C., Sorochinsky A. E., Fustero S., Soloshonok V. A., Liu H., Chem. Rev., 2014, 114, 2432

    Article  CAS  Google Scholar 

  13. Dolbier W. R., Battiste M. A., Chem. Rev., 2003, 103, 1071

    Article  CAS  Google Scholar 

  14. Fujikawa K., Fujioka Y., Kobayashi A., Amii H., Org. Lett., 2011, 13, 5560

    Article  CAS  Google Scholar 

  15. Prakash G. K. S., Ganesh S. K., Jones J. P., Kulkarni A., Masood K., Swabeck J. K., Olah G. A., Angew. Chem. Int. Ed., 2012, 51, 12090

    Article  CAS  Google Scholar 

  16. Mehta V. P., Greaney M. F., Org. Lett., 2013 15, 5036

    Article  CAS  Google Scholar 

  17. Li L., Wang F., Ni C., Hu J., Angew. Chem. Int. Ed., 2013, 52, 12390

    Article  CAS  Google Scholar 

  18. Prakash G. K. S., Krishnamoorthy S., Ganesh S. K., Kulkarni A., Haiges R., Olah G. A., Org. Lett., 2014, 16, 54

    Article  CAS  Google Scholar 

  19. Feng Z., Min Q., Xiao Y., Zhang B., Zhang X., Angew. Chem. Int. Ed., 2014, 53, 1669

    Article  CAS  Google Scholar 

  20. Wang X., Liu G., Xu X., Shibata N., Tokunaga E., Shibata N., Angew. Chem. Int. Ed., 2014, 53, 1827

    Article  Google Scholar 

  21. Ge S., Chaladaj W., Hartwig J. F., J. Am. Chem. Soc., 2014, 136, 4149

    Article  CAS  Google Scholar 

  22. Sun X., Yu S., Org. Lett., 2014, 16, 2938

    Article  CAS  Google Scholar 

  23. Xiao Y., Guo W., He G., Pan Q., Zhang X., Angew. Chem. Int. Ed., 2014, 53, 9909

    Article  CAS  Google Scholar 

  24. Williams T. J., Greaney M. F., Org. Lett., 2014, 16, 4024

    Article  CAS  Google Scholar 

  25. Araki K., Inoue M., Tetrahedron, 2013, 69, 3913

    Article  CAS  Google Scholar 

  26. Sperry J. B., Sutherland K., Org. Process Res. Dev., 2011, 15, 721

    Article  CAS  Google Scholar 

  27. Sperry J. B., Farr R. M., Levent M., Ghosh M., Hoagland S. M., Varsolona R. J., Sutherland K., Org. Process Res. Dev., 2012, 16, 1854

    Article  CAS  Google Scholar 

  28. Ou S., Jiang M., Liu J., Tetrahedron, 2013, 69, 10820

    Article  CAS  Google Scholar 

  29. Thomoson C. S., Dolbier W. R., J. Org. Chem., 2013, 78, 8904

    Article  CAS  Google Scholar 

  30. Zheng S., Kaur G., Wang H., Li M., Macnaughtan M., Yang X., Reid S., Prestegard J., Wang B., Ke H., J. Med. Chem., 2008, 51, 7673

    Article  CAS  Google Scholar 

  31. Schoenafinger K., Keil S., Urmann M., Matter H., Glien M., Wendler W., Cyclic Pyridyl-N-[1,3,4]-thiadiazol-2-yl-benzene Sulfonamides, Processes for Their Preparation and Their Use as Pharmaceuticals, WO 2009080223, 2009

    Google Scholar 

  32. Bjoere A., Bostroem J., Davidsson O., Emtenaes H., Gran U., Iliefski T., Kajanus J., Olsson R., Sandberg L., Strandlund G., Sundell J., Yuan Z. Q., Isoindoline Derivatives for the Treatment of Arrhythmias, WO 2008008022, 2008

    Google Scholar 

  33. Bender J. A., Ding M., Gentles R. G., Hewawasam P., Cyclopropyl Fused Indolobenzazepine HCV NS5B Inhibitors, US 2007270405, 2007

    Google Scholar 

  34. Frey L. F., Marcantonio K. M., Chen C., Wallace D. J., Murry J. A., Tan L., Chen W., Dolling U. H., Grabowski E. J. J., Tetrahedron, 2003, 59, 6363

    Article  CAS  Google Scholar 

  35. Furuya T., Kuttruff C., Ritter T., Curr. Opin. Drug Discovery Dev., 2008, 11, 803

    CAS  Google Scholar 

  36. Rewcastle G. W., Gamage S. A., Flanagan J. U., Frederick R., Denny W. A., Baguley B. C., Kestell P., Singh R., Kendall J. D., Marshall E. S., Lill C. L., Lee W. J., Kolekar S., Buchanan C. M., Jamieson S. M. F., Sheperd P. R., J. Med. Chem., 2011, 54, 7105

    Article  CAS  Google Scholar 

  37. Reddy M. V. B., Su C., Chiou W., Liu Y., Chen R. Y., Bastow K. F., Lee K., Wua T., Bioorganic & Medicinal Chemistry, 2008, 16, 7358

    Article  CAS  Google Scholar 

  38. Yadav V. R., Prasad S., Sung B., Aggarwal B. B., Int. Immunopharmacol., 2011, 11, 295

    Article  CAS  Google Scholar 

  39. Wyns C., Van S. K., Vanhoecke B., Deforce D., Bracke M., Heyerick A. M., Nutr. Food Res., 2012, 56, 1688

    Article  CAS  Google Scholar 

  40. Zhang Y., Srinivasan B., Xing C., Lu J., Anticancer Res., 2012, 32, 3689

    CAS  Google Scholar 

  41. Liu G., Wang X., Xu X., Lu X., Tokunaga E., Tsuzuki S., Shibata N., Org. Lett., 2013, 15, 1044

    Article  CAS  Google Scholar 

  42. Niu C., Li G., Madina, Aisa H. A., Chem. J. Chinese Universities, 2014, 35(6), 1204

    CAS  Google Scholar 

  43. Vieira L. C. C., Paixão M. W., Corrêa A. G., Tetrahedron Letters, 2012, 53, 2715

    Article  CAS  Google Scholar 

  44. Pan Y., Chen Y., Yu X., Wang J., Zhang L., He Y., Zheng Y., Zheng J. Cell. Physiol. Biochem., 2012, 29, 949

    Article  CAS  Google Scholar 

  45. Sahu N. K., Balbhadra S. S., Choudhary J., Kohli D. V., Curr. Med. Chem., 2012, 19, 209

    Article  CAS  Google Scholar 

  46. Tran T. D., Nguyen T. T., Do T. H., Huynh T. N., Tran C. D., Thai K. M., Molecules, 2012, 17, 668

    Article  Google Scholar 

  47. Shin H. J., Shon D. H., Youn H. S., Int. Immunopharmacol., 2013, 15, 38

    Article  CAS  Google Scholar 

  48. Birchall J. M., Cross G. W., Haszeldine R. N., Proc. Chem. Soc., 1960, 81

    Google Scholar 

  49. Sorochinsky A. E., Soloshonok V. A., J. Fluorine Chem., 2010, 131, 127

    Article  CAS  Google Scholar 

  50. March T. L., Johnston M. R., Duggan P. J., Org. Lett., 2012, 14, 182

    Article  CAS  Google Scholar 

  51. March T. L., Johnston M. R., Duggan P. J., Gardiner J., Chem. Biodiversity, 2012, 9, 2410

    Article  CAS  Google Scholar 

  52. Fontenelle C. Q., Conroy M., Light M., Poisson T., Pannecoucke X., Linclau B., J. Org. Chem., 2014, 79, 4186

    Article  CAS  Google Scholar 

  53. Punirun T., Soorukram D., Kuhakarn C., Reutrakul V., Pohmakotr M., Eur. J. Org. Chem., 2014, 4162

    Google Scholar 

  54. Mortensen D. S., Rodriguez A. L., Carlson K. E., Sun J., Katzenellenbogen B. S., Katzenellenbogen J. A., J. Med. Chem., 2001, 33, 3838

    Article  Google Scholar 

  55. Shi G. Q., Dropinski J. F., Zhang Y., Santini C., Sahoo S. P., Berger J. P., MacNaul K., Zhou G., Agrawal A., Alvaro R., Cai T. Q., Hernandez M., Wright S. D., Moller D. E., Heck J. V., Meinke P. T., J. Med. Chem., 2005, 48, 5589

    Article  CAS  Google Scholar 

  56. Wang X., Lu Y., Dai H. X., Yu J. Q., J. Am. Chem. Soc., 2010, 132, 12203

    Article  CAS  Google Scholar 

  57. Coy B. E. D., Jovanovic L., Sefkow M., Org. Lett., 2010, 12, 1976

    Article  Google Scholar 

  58. Mangas-Sánchez J., Busto E., Gotor-Fernández V., Gotor V., Org. Lett., 2010, 12, 3498

    Article  Google Scholar 

  59. Liu Y., Lu A., Hu K., Wang Y., Song H., Zhou Z., Tang C., Eur. J. Org. Chem., 2013, 4836

    Google Scholar 

  60. Ando M., Wada T., Sato N., Org. Lett., 2006, 8, 3805

    Article  CAS  Google Scholar 

  61. Birchall J. M., Cross G. W., Haszeldine R. N., Proc. Chem. Soc., 1960, 81

    Google Scholar 

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. China

    Wei Wang, Mingqing Hua, Yan Huang, Qi Zhang, Xiaoyan Zhang & Jingbo Wu

  2. Hainan Provincial Key Laboratory of Fine Chemistry, Hainan University, Haikou, 570228, P. R. China

    Qi Zhang

Authors
  1. Wei Wang
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  2. Mingqing Hua
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  3. Yan Huang
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  4. Qi Zhang
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  5. Xiaoyan Zhang
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  6. Jingbo Wu
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Corresponding authors

Correspondence to Mingqing Hua or Qi Zhang.

Additional information

Supported by the National Natural Science Foundation of China(Nos.21302071, 21261008, 21204031), the Natural Science Foundation of Jiangsu Province, China(No.BK20130484), the Scientific Research Foundation for Advanced Talents of Jiangsu University, China(No.12JDG089/14JDG054) and the Hainan International Science and Technology Cooperation, China (No.KJHZ2014-05).

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Wang, W., Hua, M., Huang, Y. et al. Difluoromethylation of 2-hydroxychalcones using sodium 2-chloro-2,2-difluoroacetate as difluoromethylating agent. Chem. Res. Chin. Univ. 31, 362–366 (2015). https://doi.org/10.1007/s40242-015-4456-0

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  • DOI: https://doi.org/10.1007/s40242-015-4456-0

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