Efficient access to extended yagupolskii-umemoto-type reagents: Triflic acid catalyzed intramolecular cyclization of ortho- ethynylaryltrifluoromethylsulfanes

Angewandte Chemie - International Edition

Volumn 49, Issue 3, 2010, Pages 572-576

  Matsnev, Andrej ^a   Noritake, Shun ^a   Nomura, Yoshinori ^a   Tokunaga, Etsuko ^a   Nakamura, Shuichi ^a   Shibata, Norio ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

C c bond formation; Cyclization; Fluorine; Triflic acid; Trifluoromethylation

Indexed keywords

C-C BOND FORMATION; INTRAMOLECULAR CYCLIZATIONS; KETO ESTER; TRIFLIC ACIDS; TRIFLUOROMETHYL; TRIFLUOROMETHYLATION;

ACIDS; ESTERS; FLUORINE;

CYCLIZATION;

ETHYLENE; ETHYLENE DERIVATIVE; MESYLIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

CATALYSIS; CYCLIZATION; ETHYLENES; MESYLATES; MOLECULAR STRUCTURE;

EID: 74549179204     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905225     Document Type: Article

References (53)

1. a) P. Kirsch, Modern Fluoroorganic Chemistry; Wiley-VCH, Weinheim, 2004;
2. b) T. Umemoto, Chem. Rev. 1996, 96, 1757-1777;
3. c) A. M. Thayer, Chem Eng. News 2006, 84, 15-24.
4. a) G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786;
5. b) R. P. Shigh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632;
6. c) T. Billard, B. R. Langlois, Eur. J. Org. Chem. 2007, 891-897;
7. d) J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR1 -PR43;
8. e) N. Shibata, S. Mizuta. T. Toru, J. Synth. Org. Chem. Jpn. 2008, 66, 215-218;
9. f) N. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry 2008, 19, 2633-2644.
10. L. M. Yagupol'skii, N. V. Kondratenko, G. N. Timofeeva, J. Org. Chem. USSR 1984, 20, 103-106.
11. a) T. Umemoto, S. Ishihara, Tetrahedron Lett. 1990, 31, 3579-3582;
12. b) T. Umemoto, S. Ishihara, J. Am. Chem. Soc. 1993, 115, 2156-2164;
13. c) J.-J. Yang, R. L. Kirchmeier, J. M. Shreeve, J. Org. Chem. 1998, 63, 2656-2660;
14. d) L. M. Yagupolskii, V. A. Matsnev, R. K. Orlova, B. G. Deryabkin, Y. L. Yagupolskii, J. Fluorine Chem. 2008, 129, 131-136;
15. e) L. M. Yagupolskii, I. I. Maletina, N. V. Kondratenko, V. V. Orda, Synthesis 1978, 835-837.
16. a) E. Magnier, J. C. Blazejewski, M. Tordeux, C. Wakselman, Angew. Chem 2006, 118, 1301-1304;
17. Angew. Chem. Int. Ed. 2006, 45, 1279-1282;
18. b) Y. Macé, B. Raymondeau, C. Pradet, J.-C. Blazejewski, E. Magnier, Eur. J. Org. Chem. 2009, 1390-1397.
19. a) P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586;
20. b) I. Kieltsch., P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768-771;
21. Chem. Int. Ed. 2007, 46, 754-757;
22. c) P. Eisenberger, I. Kieltsch, N. Armanino, A. Togni, Chem. Commun. 2008, 13, 1575-1577;
23. d) I. Kieltsch, P. Eisenberger, K. Stanek, A. Togni, Chimia 2008, 62, 260-263;
24. e) K. Stanek, R. Koller, A. Togni, J. Org. Chem. 2008, 73, 7678-7685;
25. f) R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, R. Koller, A. Togni, Angew. Chem. 2009, 121, 4396-4400;
26. Angew. Chem. Int. Ed. 2009, 48, 4332-4336;
27. g) R. Koller, Q. Huchet, P. Battaglia, J.-M. Welch, A. Togni, Chem. Commun. 2009, 5993-5995.
28. S. Noritake, N. Shibata, S. Nakamura, T. Toru, M. Shiro, Eur. J. Org. Chem. 2008, 3465-3468.
29. Tokyo Chemical Industry Co., Ltd., O0366 R-5093, 2009.
30. a) N. Shibata, J. Synth. Org. Chem. Jpn. 2006, 64, 14-24;
31. b) N. Shibata, T. Ishimaru, S. Nakamura, T. Toru, J. Fluorine Chem. 2007, 128, 469-483;
32. c) N. Shibata, E. Suzuki, T. Asahi, M. Shiro, J. Am. Chem. Soc. 2001, 123, 7001-7009;
33. d) N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2005, 117, 4276-4279;
34. Angew. Chem. Int. Ed. 2005, 44, 4204-4207;
35. e) D. S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, Angew. Chem. 2008, 120, 170-174;
36. Angew. Chem. Int. Ed. 2008, 47,164-168;
37. f) T. Fukuzumi, N. Shibata, M. Sugiura, H. Yasui, S. Nakamura, T. Toru, Angew. Chem. 2006, 118, 5095-5099;
38. Angew. Chem. Int. Ed. 2006, 45, 4973-4977;
39. g) S. Mizuta, N. Shibata, Y. Goto, T. Furukawa, S. Nakamura, T. Toru, J. Am. Chem. Soc. 2007, 129, 6394-6395;
40. h) S. Mizuta, N. Shibata, S. Akiti, H. Fujimoto, S. Nakamura, T. Toru, Org. Lett. 2007, 9, 3707-3710;
41. i) S. Noritake, N. Shibata, Y. Nomura, Y. Huang, A. Matsnev, S. Nakamura, T. Toru, D. Cahard, Org. Biomol. Chem. 2009, 7, 3599-3604.
42. a) R. C. Larock in Acetylene Chemistry. Chemistry, Biology, and Material Science (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, New York, 2005, chap. 2, pp. 51-99;
43. b) R. C. Larock, Top. Organomet. Chem. 2005, 14, 147-182.
44. R. C. Larock, D. Yue, Tetrahedron Lett. 2001, 42, 6011-6013.
45. a) C. D. Jones, M. G. Jevnikar, A. J. Pike, M. K. Peters, L. J. Black, A. R. Thompson, J. F. Falcone, J. A. Clemens, J. Med. Chem. 1984, 27, 1057-1066;
46. b) M. Raga, C. Palacin, J. M. Castello, J. A. Ortiz, M. R. Cuberes, M. Moreno-Manas, Eur. J. Med. Chem. 1986, 21, 329-332.
47. a) I. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585-4587;
48. Angew. Chem. Int. Ed. 2006, 45, 4473-4475;
49. b) I. Nakamura, T. Sato, M. Terada, Y. Yamamoto, Org. Lett. 2008, 10, 2649-2651.
50. T. Kitamura, T. Tkkachi, M. Miyaji, H. Kawasato, H. Taniguchi, J. Chem. Soc. Perkin Trans 1 1994, 1907-1911.
51. Just before the completion of this work, triflic acid catalyzed synthesis of spirocyles has appeared. T. Jin, M. Himuro, Y. Yamamoto, Angew. Chem. 2009, 121, 6007-6010;
52. Angew. Chem. Int. Ed. 2009, 48, 5893-5896.
53. J. H. Kaldis, P. Morawietz, M. J. McGlinchey, Organometallics 2003, 22, 1293-1301.