Synthesis 2020; 52(08): 1203-1210
DOI: 10.1055/s-0039-1690054
feature
© Georg Thieme Verlag Stuttgart · New York

Oxidation of 4-Aryl-1,1,1-trifluorobut-2-en-2-yl Trifluoro­methanesulfonates by 4-Picoline-N-Oxide: A Novel Approach to β-Trifluoromethyl-α,β-enones

Dong Li
,
Shujun Lv
,
Jingping Qu
,
Yuhan Zhou
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China   Email: zhouyh@dl.cn
› Author Affiliations
Financial support for this work was provided by the National Natural Science Foundation of China (No. 21878037).
Further Information

Publication History

Received: 28 October 2019

Accepted after revision: 19 January 2020

Publication Date:
10 February 2020 (online)


Abstract

An efficient approach to β-trifluoromethyl-α,β-enones via oxidation of 4-aryl-1,1,1-trifluorobut-2-en-2-yl trifluoromethanesulfonates is described. The reaction proceeds smoothly under mild and metal­-free conditions and tolerates a wide range of functional groups. Various β-trifluoromethyl-α,β-enones were obtained in moderate to good yields.

Supporting Information

 
  • References

    • 1a Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
    • 1b Hagmann WK. J. Med. Chem. 2008; 51: 4359
    • 1c Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2005; 44: 214
    • 1d Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Aceña JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
    • 2a Obijalska E, Pawelec M, Mlostoń G, Capperucci A, Tanini D, Heimgartner H. Eur. J. Org. Chem. 2018; 3716
    • 2b Huang B, Li C, Wang H, Wang C, Liu L, Zhang J. Org. Lett. 2017; 19: 5102
    • 3a Boreux A, Lambion A, Campeau D, Sanita M, Coronel R, Riant O, Gagosz F. Tetrahedron 2018; 74: 5232
    • 3b Davies AT, Taylor JE, Douglas J, Collett CJ, Morrill LC, Fallan C, Slawin AM. Z, Churchill G, Smith AD. J. Org. Chem. 2013; 78: 9243
    • 4a Wang W, Lian X, Chen D, Liu X, Lin L, Feng X. Chem. Commun. 2011; 47: 7821
    • 4b Leuger J, Blond G, Billard T, Haufe G, Langlois BR. J. Fluorine Chem. 2011; 132: 799
    • 4c Blay G, Fernández I, Muñoz MC, Pedro JR, Vila C. Chem. Eur. J. 2010; 16: 9117
    • 5a Chai G, Sun A, Zhai D, Wang J, Deng W, Wong HN. C, Chang J. Org. Lett. 2019; 21: 5040
    • 5b Bai D, Wang X, Zheng G, Li X. Angew. Chem. Int. Ed. 2018; 57: 6633
    • 5c You Y, Lu W, Wang Z, Chen Y, Xu X, Zhang X, Yuan W. Org. Lett. 2018; 20: 4453
    • 6a Yamazaki T, Kawasaki-Takasuka T, Furuta A, Sakamoto S. Tetrahedron 2009; 65: 5945
    • 6b Watanabe Y, Yamazaki T. J. Org. Chem. 2011; 76: 1957
    • 6c Yamazaki T, Ichige T, Kitazume T. Org. Lett. 2004; 6: 4073
    • 6d Ramasamy M, Lin H, Kuo S, Hsieh M. Synlett 2019; 30: 356
  • 7 Xu Y, Dolbier WR. Jr. Tetrahedron Lett. 1998; 39: 9151
    • 8a Zhao Y, Zhou Y, Liu J, Yang D, Tao L, Liu Y, Dong X, Liu J, Qu J. J. Org. Chem. 2016; 81: 4797
    • 8b Zhao Y, Zhou Y, Zhang C, Wang H, Zhao J, Jin K, Liu J, Liu J, Qu J. Org. Biomol. Chem. 2017; 15: 5693
    • 8c Zhao Y, Zhou Y, Zhang C, Li D, Sun P, Li J, Wang H, Liu J, Qu J. J. Org. Chem. 2018; 83: 2858
    • 8d Li D, Zhou Y, Zhao Y, Zhang C, Li J, Zhao J, Qu J. J. Fluorine Chem. 2018; 212: 122
    • 8e Zhou Y, Zhang C, Zhao Y, Li D, Zhao J, Wang Z, Qu J. Eur. J. Org. Chem. 2018; 6217
    • 9a Medley JW, Movassaghi M. J. Org. Chem. 2009; 74: 1341
    • 9b Londregan AT, Jennings S, Wei L. Org. Lett. 2010; 12: 5254
    • 10a Martinez-Erro S, Sanz-Marco A, Gómez AB, Vázquez-Romero A, Ahlquist MS. G, Martín-Matute B. J. Am. Chem. Soc. 2016; 138: 13408
    • 10b Hamada Y, Kawasaki-Takasuka T, Yamazaki T. Beilstein J. Org. Chem. 2017; 13: 1507
  • 11 Kazakova AN, Iakovenko RO, Boyarskaya IA, Nenajdenko VG, Vasilyev AV. J. Org. Chem. 2015; 80: 9506
  • 12 Stark DG, Morrill LC, Yeh P, Slawin AM. Z, O’Riordan TJ. C, Smith AD. Angew. Chem. Int. Ed. 2013; 52: 11642