Iron-catalyzed 1,2-addition of perfluoroalkyl iodides to alkynes and alkenes

Angewandte Chemie - International Edition

Volumn 53, Issue 19, 2014, Pages 4910-4914

  Xu, Tao ^a   Cheung, Chi Wai ^a   Hu, Xile ^a  

^a EPFL   (Switzerland)

Author keywords

alkyne; cross coupling; fluorine; iron; synthetic methods

Indexed keywords

CATALYSIS; FLUORINE; IRON;

ALKENYL; ALKYNE; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; FUNCTIONALIZED; IRON CATALYSIS; ORGANIC MOLECULES; SYNTHETIC METHODS;

HYDROCARBONS;

ALKENE; ALKYNE; IODIDE; IRON;

CATALYSIS; CHEMISTRY;

ALKENES; ALKYNES; CATALYSIS; IODIDES; IRON;

EID: 84899837826     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201402511     Document Type: Article

References (79)

1. R. Filler, Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Elsevier, Amsterdam, 1982
2. Fluorine in Bioorganic Chemistry (Eds.:, J. T. Welch, S. Eswarakrishman,), Wiley, New York, 1991
3. M. Hird, Chem. Soc. Rev. 2007, 36, 2070
4. K. L. Kirk, Org. Process Res. Dev. 2008, 12, 305.
5. J. H. Clark, D. Wails, T. W. Bastock, Aromatic Fluorination, CRC, Boca Raton, 1996
6. J. A. Gladysz, I. Horvath, D. P. Curran, Handbook of Fluorous Chemistry, Wiley-VCH, Weinheim, 2004
7. P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004
8. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006
9. J. P. Bégué; D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley-Interscience, Hoboken, 2008
10. I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, 2009
11. V. A. Petrov, Fluorinated Heterocyclic Compounds: Synthesis Chemistry and Applications, Wiley, Hoboken, 2009.
12. M. K. McClinton, Tetrahedron 1992, 48, 6555
13. M. Schlosser, Angew. Chem. 2006, 118, 5558
14. Angew. Chem. Int. Ed. 2006, 45, 5432
15. J.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975
16. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
17. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1
18. O. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475.
19. A. Studer, Angew. Chem. 2012, 124, 9082
20. Angew. Chem. Int. Ed. 2012, 51, 8950
21. P. Chen, G. Liu, Synthesis 2013, 45, 2919; For selected recent examples, see
22. A. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286
23. Angew. Chem. Int. Ed. 2011, 50, 9120
24. J. Xu, Y. Fu, D. Luo, Y. Jiang, B. Xiao, Z. Liu, T. Gong, L. Liu, J. Am. Chem. Soc. 2011, 133, 15300
25. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410
26. X. Mu, T. Wu, H.-Y. Wang, Y.-L. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878
27. X. Wu, L. Chu, F. Qing, Angew. Chem. 2013, 125, 2254
28. Angew. Chem. Int. Ed. 2013, 52, 2198
29. S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, V. Gouverneur, J. Am. Chem. Soc. 2013, 135, 2505
30. H. Egami, R. Shimizu, S. Kawamura, M. Sodeoka, Angew. Chem. 2013, 125, 4092
31. Angew. Chem. Int. Ed. 2013, 52, 4000
32. H. Egami, S. Kawamura, A. Miyazaki, M. Sodeoka, Angew. Chem. 2013, 125, 7995
33. Angew. Chem. Int. Ed. 2013, 52, 7841
34. Z.-M. Chen, W. Bai, S.-H. Wang, B.-M. Yang, Y.-Q. Tu, F.-M. Zhang, Angew. Chem. 2013, 125, 9963
35. Angew. Chem. Int. Ed. 2013, 52, 9781.
36. P. G. Janson, I. Ghoneim, N. O. Ilchenko, K. J. Szabõ, Org. Lett. 2012, 14, 2882
37. Y. Li, A. Studer, Angew. Chem. 2012, 124, 8345
38. Angew. Chem. Int. Ed. 2012, 51, 8221
39. Y. Yasu, T. Koike, M. Akita, Angew. Chem. 2012, 124, 9705
40. Angew. Chem. Int. Ed. 2012, 51, 9567
41. R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462.
42. F. Wang, X. Qi, Z. Liang, P. Chen, G. Liu, Angew. Chem. 2014, 126, 1912
43. Angew. Chem. Int. Ed. 2014, 53, 1881.
44. 3I per gram from Sigma-Aldrich are 50, 100, 18, and 7 USD, respectively. For more information, see: http://www.sigmaaldrich.com.
45. Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034
46. P. V. Pham, D. A. Nagib, D. W. C. MacMillan, Angew. Chem. 2011, 123, 6243
47. Angew. Chem. Int. Ed. 2011, 50, 6119
48. Y. Itoh, K. Mikami, Org. Lett. 2005, 7, 4883
49. T. Kitazume, N. Ishikawa, J. Am. Chem. Soc. 1985, 107, 5186
50. Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95.
51. A. Hafner, A. Bihlmeier, M. Nieger, W. Klopper, S. Bräse, J. Org. Chem. 2013, 78, 7938
52. A. Hafner, T. J. Feuerstein, S. Bräse, Org. Lett. 2013, 15, 3468
53. R. Zeng, C. Fu, S. Ma, Angew. Chem. 2012, 124, 3954
54. Angew. Chem. Int. Ed. 2012, 51, 3888
55. Q. Qi, Q. Shen, L. Lu, J. Am. Chem. Soc. 2012, 134, 6548
56. A. T. Herrmann, L. L. Smith, A. Zakarian, J. Am. Chem. Soc. 2012, 134, 6976.
57. X. Fang, X. Yang, X. Yang, S. Mao, Y. Wang, G. Chen, F. Wu, Tetrahedron 2007, 63, 10684
58. Y. Takeyama, Y. Ichinose, K. Oshima, K. Utimato, Tetrahedron Lett. 1989, 30, 3159
59. Y. Li, H. Li, J. Hu, Tetrahedron 2009, 65, 478
60. W. Huang, L. Lv, Y. Zhang, Chin. J. Chem. 1990, 4, 350
61. K. Tsuchii, M. Imura, N. Kamada, T. Hirao, A. Ogawa, J. Org. Chem. 2004, 69, 6658; For some other methods, see
62. T. Ishihara, M. Kuroboshi, Y. Okada, Chem. Lett. 1986, 1895
63. S. Ma, X. Lu, Tetrahedron 1990, 46, 357
64. M. P. Jennings, E. A. Cork, P. V. Ramachandran, J. Org. Chem. 2000, 65, 8763.
65. C. J. Wallentin, J. D. Nguyen, P. Finkbeiner, C. R. J. Stephenson, J. Am. Chem. Soc. 2012, 134, 8875
66. N. Iqbal, J. Jung, S. Park, E. J. Cho, Angew. Chem. 2014, 126, 549
67. Angew. Chem. Int. Ed. 2014, 53, 539.
68. n] as the catalyst for similar addition reactions, see:, I. Ojima, 1991, Patent No. US5017718A. Only a small number of relatively simple terminal alkenes and alkynes were employed as substrates.
69. 3-catalyzed reaction, see:, Y.-F. Liang, N. Jiao, Angew. Chem. 2014, 126, 558
70. Angew. Chem. Int. Ed. 2014, 53, 548.
71. Q. Chen, Y. He, Z. Yang, J. Fluorine Chem. 1986, 34, 255
72. Z. Yang, D. J. Burton, J. Chem. Soc. Chem. Commun. 1992, 233
73. C. R. Davis, D. J. Burton, Z. Yang, J. Fluorine Chem. 1995, 70, 135
74. T. Takagi, T. Kanamori, J. Fluorine Chem. 2011, 132, 427
75. M. Slodowicz, S. Barata-Vallejo, A. Vazquez, N. S. Nudelman, A. Postigo, J. Fluorine Chem. 2012, 135, 137.
76. B. Scheiper, M. Bonnekessel, H. Krause, A. Furstner, J. Org. Chem. 2004, 69, 3943
77. C. G. Bates, P. Saejueng, M. Q. Doherty, D. Venkataraman, Org. Lett. 2004, 6, 5005
78. C. W. Cheung, P. Ren, X. Hu, submitted.
79. For cyclization reactions with perfluoroalkyl iodides, see ref. [9c] and, K. Tsuchii, Y. Ueta, N. Kamada, Y. Einaga, A. Nomoto, A. Ogawa, Tetrahedron Lett. 2005, 46, 7275.