Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations

Advanced Synthesis and Catalysis

Volumn 349, Issue 17-18, 2007, Pages 2610-2618

  Bielawski, Marcin ^a   Zhu, Mingzhao ^a   Olofsson, Berit ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Arenes; Aromatic substitution; Diaryliodonium salts; Hypervalent compounds; Iodine; Oxidation

Indexed keywords

EID: 37349091138     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700373     Document Type: Article

References (52)

1. T. Wirth, Angew. Chem. Int. Ed. 2005, 44, 3656-3665.
2. P. J. Stang, J. Org. Chem. 2003, 68, 2997-3008.
3. a) T. Wirth, Angew. Chem. Int. Ed. Engl. 2001, 40, 2812-2814;
4. b) K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245-2258.
5. a) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584;
6. b) A. Varvoglis, Tetrahedron 1997, 53, 1179-1255.
7. V. K. Aggarwal, B. Olofsson, Angew. Chem. Int. Ed. 2005, 44, 5516-5519.
8. a) P. Gao, P. S. Portoghese, J. Org. Chem. 1995, 60, 2276-2278;
9. b) J. H. Ryan, P. J. Stang, Tetrahedron Lett. 1997, 38, 5061-5064;
10. c) F. M. Beringer, W. J. Daniel, S. A. Galton, G. Rubin, J. Org. Chem. 1966, 31, 4315-4318.
11. S.-K. Kang, T. Yamaguchi, T.-H. Kim, P.-S. Ho, J. Org. Chem. 1996, 61, 9082-9083.
12. N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924-1935.
13. D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.
14. T. Kitamura, M. Yamane, K. Inoue, M. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674-11679.
15. Y. Toba, J. Photopolym. Sci. Technol. 2003, 16, 115-118.
16. C. H. Oh, J. S. Kim, H. H. Jung, J. Org. Chem. 1999, 64, 1338-1340.
17. a) M. Ochiai, M. Toyonari, T. Nagaoka, D.-W. Chen, M. Kida, Tetrahedron Lett. 1997, 38, 6709-6712;
18. b) V. W. Pike, F. Butt, A. Shah, D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1 1999, 245-248;
19. c) T. Kitamura, J. Matsuyuki, H. Taniguchi, Synthesis 1994, 147-148;
20. d) T. Kitamura, M. Kotani, Y. Fujiwara, Tetrahedron Lett. 1996, 37, 3721-3722;
21. e) V. V. Zhdankin, M. C. Scheuller, P. J. Stang, Tetrahedron Lett. 1993, 34, 6853-6856;
22. f) G. F. Koser, R. H. Wettach, C. S. Smith, J. Org. Chem. 1980, 45, 1543-1544.
23. a) T. Kitamura, J. Matsuyuki, K. Nagata, R. Furuki, H. Taniguchi, Synthesis 1992, 945-946;
24. b) A. Shah, V. W. Pike, D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1 1997, 2463-2465;
25. c) M. A. Carroll, V. W. Pike, D. A. Widdowson, Tetrahedron Lett. 2000, 41, 5393-5396.
26. a) P. J. Stang, V. V. Zhdankin, R. Tykwinski, Tetrahedron Lett. 1992, 33, 1419-1422;
27. b) P. J. Stang, V. V. Zhdankin, R. Tykwinski, N. S. Zefirov, Tetrahedron Lett. 1991, 32, 7497-7498;
28. c) N. S. Zefirov, T. M. Kasumov, A. S. Koz'min, V. D. Sorokin, P. J. Stang, V. V. Zhdankin, Synthesis 1993, 1209-1210.
29. F. M. Beringer, R. A. Falk, M. Karniol, I. Lillien, G. Masulio, M. Mausner, E. Sommer, J. Am. Chem. Soc. 1959, 81, 342-351.
30. T. Iwama, V. B. Birman, S. A. Kozmin, V. H. Rawal, Org. Lett. 1999, 1, 673-676.
31. M. D. Hossain, T. Kitamura, Tetrahedron 2006, 62, 6955-6960.
32. M. D. Hossain, T. Kitamura, J. Org. Chem. 2006, 71, 9903-9905.
33. A. Kryska, L. Skulski, Molecules 2001, 6, 875-880.
34. P. Kazmierczak, L. Skulski, Synthesis 1995, 1027-1032.
35. M. Bielawski, B. Olofsson, Chem. Commun. 2007, 2521-2523.
36. a) T. K. Page, T. Wirth, Synthesis 2006, 3153-3155;
37. b) J. Pavlinac, M. Zupan, S. Stavber, Synthesis 2006, 2603-2607.
38. a) T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita, Angew. Chem. Int. Ed. 2005, 44, 6193-6196;
39. b) M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto, J. Am. Chem. Soc. 2005, 127, 12244-12245;
40. c) Y. Yamamoto, H. Togo, Synlett 2006, 798-800.
41. Commercial mCPBA was used after drying. The exact amount of oxidant was determined by titration.
42. Full optimization details are given in the Supporting Information.
43. 3 to wash away the formed mCBA. Surprisingly, this instead resulted in isolation of salt 3a with mCBA as anion.
44. D. Bykowski, R. Mcdonald, R. J. Hinkle, R. R. Tykwinski, J. Org. Chem. 2002, 67, 2798-2804.
45. A complete list of arenes and aryl iodides that failed to give iodonium salts can be found in the Supporting Information.
46. N. S. Pirguliyev, V. K. Brel, N. G. Akhmedov, N. S. Zefirov, Synthesis 2000, 81-83.
47. For the synthesis and use of 3af, see B. Olofsson, V. K. Aggarwal, Proc. 2nd Int. Conf. on Hypervalent Iodine, 2006, 47-50. The attempts to synthesize salt 3ag are unpublished.
48. M. D. Hossain, T. Kitamura, Tetrahedron 2006, 47, 7889-7891.
49. Iodobenzene was detected in reactions with short reaction time, supporting the assumption that iodobenzene is an intermediate in the reaction.
50. The formation of lithium triflate complicated the isolation of salt 3a, and purification was thus performed with flash chromatography instead of precipitation.
51. For example, benzene + chlorobenzene; benzene + toluene or benzene + anisole.
52. A. I. Vogel, B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith, A. R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, Longman, London, New York, 1978, 1280 pp.