Synlett 2015; 26(01): 36-39
DOI: 10.1055/s-0034-1378651
cluster
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Synthesis of Difluoromethylated Arenes

Peng Xu
a   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: ptang@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, P. R. of China   Fax: +86(22)23508957
,
Shuo Guo
a   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: ptang@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, P. R. of China   Fax: +86(22)23508957
,
Liyan Wang
a   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: ptang@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, P. R. of China   Fax: +86(22)23508957
,
Pingping Tang*
a   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: ptang@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, P. R. of China   Fax: +86(22)23508957
› Author Affiliations
Further Information

Publication History

Received: 16 July 2014

Accepted: 24 July 2014

Publication Date:
21 August 2014 (online)


Abstract

The growing importance of fluorinated compounds in pharmaceuticals, agrochemicals, and materials has triggered the development of new methods for the introduction of fluorine into small molecules. Although it is a challenge to prepare fluorinated compounds, new developed reactions are addressing this challenge and facilitating the synthesis of difluoromethylated arenes. In this article, we highlight recently important developments in the synthesis of difluoromethylated arenes.

1 Introduction

2 Cross-Coupling with Copper

3 Cross-Coupling with Palladium

4 Cross-Coupling with Other Metals

5 C(sp2)–H Activation

6 C(sp3)–H Activation

7 Conclusion

 
  • References

    • 1a Erichson JA, McLoughlin JI. J. Org. Chem. 1995; 60: 1626
    • 1b Knust H, Achermann G, Ballard T, Buettelmann B, Gasser R, Fischer H, Hernandez M.-C, Knoflach F, Koblet A, Stadler H, Thomas AW, Trube G, Waldmeier P. Bioorg. Med. Chem. Lett. 2009; 19: 5940
    • 1c Meanwell NA. J. Med. Chem. 2011; 54: 2529 ; and references cited therein
    • 2a Markovski LN, Pahinnik VE, Kirsanov AV. Synthesis 1973; 787
    • 2b Middleton WJ. J. Org. Chem. 1975; 40: 574
    • 2c Singh RP, Sheeve JM. J. Org. Chem. 2003; 68: 6063
    • 2d Umemoto T, Singh RP, Xu Y, Saito N. J. Am. Chem. Soc. 2010; 132: 18199

      For the latest selected reviews, see:
    • 3a Hu J, Zhang W, Wang F. Chem. Commun. 2009; 7465
    • 3b Liang T, Neumann C, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
  • 4 Fujikawa K, Fujioka Y, Kobayashi A, Amii H. Org. Lett. 2011; 13: 5560
  • 5 Feng Z, Chen F, Zhang X. Org. Lett. 2012; 14: 1938
  • 6 Fier PS, Hartwig JF. J. Am. Chem. Soc. 2012; 134: 5524
  • 7 Surya Prakash GK, Ganesh SK, Jones JP, Kulkarni A, Masood K, Swabeck JK, Olah GA. Angew. Chem. Int. Ed. 2012; 51: 12090
  • 8 Qi Q, Shen Q, Lu L. J. Am. Chem. Soc. 2012; 134: 6548
  • 9 Jiang X, Chen Z, Xu X, Qing F. Org. Chem. Front. 2014; 1: 774
  • 10 Min Q, Yin Z, Feng Z, Guo W, Zhang X. J. Am. Chem. Soc. 2014; 136: 1230
  • 11 Feng Z, Min Q, Xiao Y, Zhang B, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 1669
  • 12 Guo C, Wang R, Qing F. J. Fluorine Chem. 2012; 143: 135
  • 13 Ge S, Chaladaj W, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4149
  • 14 Yin F, Wang Z, Li Z, Li C. J. Am. Chem. Soc. 2012; 134: 10401
  • 15 Mizuta S, Stenhagen IS. R, O’Duill M, Wolstenhulme J, Kirjavainen AK, Forsback SJ, Tredwell M, Sandford G, Moore PR, Huiban M, Luthra SK, Passchier J, Solin O, Gouverneur V. Org. Lett. 2013; 15: 2648
  • 16 Araki K, Inoue M. Tetrahedron 2013; 69: 3913
  • 17 Ohtsuka Y, Yamakawa T. Tetrahedron 2011; 67: 2323
  • 18 Fujiwara Y, Dixon JA, Rodriguez RA, Baxter RD, Dixon DD, Collins MR, Blackmond DG, Baran PS. J. Am. Chem. Soc. 2012; 134: 1494
  • 19 Zhou Q, Ruffoni A, Gianatassio R, Fujiwara Y, Sella E, Shabat D, Baran PS. Angew. Chem. Int. Ed. 2013; 52: 3949
  • 20 Su Y, Hou Y, Yin F, Xu Y, Li Y, Zheng X, Wang X. Org. Lett. 2014; 16: 2958
  • 21 Xia J, Zhu C, Chen C. J. Am. Chem. Soc. 2013; 135: 17494
  • 22 Xu P, Guo S, Wang L, Tang P. Angew. Chem. Int. Ed. 2014; 53: 5955