Catalytic generation of arynes and trapping by nucleophilic addition and iodination

Angewandte Chemie - International Edition

Volumn 51, Issue 14, 2012, Pages 3368-3372

  Hamura, Toshiyuki ^a   Chuda, Yu ^a   Nakatsuji, Yuya ^a   Suzuki, Keisuke ^b  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

arenes; arynes; iodine; lithiation; regioselectivity

Indexed keywords

ARENES; ARYNES; BENZYNE; FAIR EXCHANGE; IODOARENES; LITHIATION; NUCLEOPHILIC ADDITIONS;

ADDITION REACTIONS; LITHIUM; NUCLEOPHILES; REGIOSELECTIVITY;

IODINE;

EID: 84859230217     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108415     Document Type: Article

References (50)

1. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic, New York, 1967
2. S. V. Kessar, in Comprehensive Organic Synthesis, Vol. 4 (Ed.:, B. M. Trost,), Pergamon, Oxford, UK, 1991, pp. 483-515
3. H. Pellissier, M. Santelli, Tetrahedron 2003, 59, 701-730
4. H. H. Wenk, M. Winkler, W. Sander, Angew. Chem. 2003, 115, 518-546
5. Angew. Chem. Int. Ed. 2003, 42, 502-528.
6. T. Kitamura, M. Yamane, K. Inoue, M. Tokuda, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674-11679
7. I. Sapountzis, W. Lin, M. Fisher, P. Knochel, Angew. Chem. 2004, 116, 4464-4466
8. Angew. Chem. Int. Ed. 2004, 43, 4364-4366
9. Z. Liu, R. C. Larock, Org. Lett. 2004, 6, 99-102
10. M. Uchiyama, T. Miyoshi, Y. Kajihara, T. Sakamoto, Y. Otani, T. Ohwada, Y. Kondo, J. Am. Chem. Soc. 2002, 124, 8514-8515
11. M. Uchiyama, Y. Kobayashi, T. Furuyama, S. Nakamura, Y. Kajihara, T. Miyoshi, T. Sakamoto, Y. Kondo, K. Morokuma, J. Am. Chem. Soc. 2008, 130, 472-480.
12. T. Matsumoto, T. Hosoya, M. Katsuki, K. Suzuki, Tetrahedron Lett. 1991, 32, 6735-6736
13. T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki, J. Am. Chem. Soc. 1994, 116, 1004-1015
14. T. Hamura, T. Arisawa, T. Matsumoto, K. Suzuki, Angew. Chem. 2006, 118, 6996-6998
15. Angew. Chem. Int. Ed. 2006, 45, 6842-6844.
16. J. Clayden, Organolithiums: Selectivity for Synthesis, Vol. 23, Pergamon, Oxford, 2002, pp. 111-147 (Tetrahedron Organic Chemistry Series)
17. P. Beak, D. J. Allen, J. Am. Chem. Soc. 1992, 114, 3420-3425
18. C. Nájera, J. M. Sansano, M. Yus, Tetrahedron 2003, 59, 9255-9303
19. M. Da̧browski, J. Kubicka, S. Lulinski, J. Serwatowski, Tetrahedron 2005, 61, 6590-6595.
20. D. Astruc, Modern Arene Chemistry, Wiley-VCH, Weinheim, 2002
21. C. B. de Koning, A. L. Rousseau, W. A. L. van Otterlo, Tetrahedron 2003, 59, 7-36.
22. G. Wittig, R. W. Hoffmann, Chem. Ber. 1962, 95, 2729-2734
23. A. I. Meyers, P. D. Pansegrau, Tetrahedron Lett. 1983, 24, 4935
24. A. I. Meyers, P. D. Pansegrau, J. Chem. Soc. Chem. Commun. 1985, 690
25. C.-J. F. Du, H. Hart, K.-K. D. Ng, J. Org. Chem. 1986, 51, 3162-3165
26. T. Ghosh, H. Hart, J. Org. Chem. 1988, 53, 3555-3558
27. A. Saednya, H. Hart, Synthesis 1996, 1455
28. S. Tripathy, R. LeBlanc, T. Durst, Org. Lett. 1999, 1, 1973-1975
29. S. Tripathy, H. Hussain, T. Durst, Tetrahedron Lett. 2000, 41, 8401-8405
30. H. Tomori, J. M. Fox, S. L. Buchwald, J. Org. Chem. 2000, 65, 5334-5341
31. F. Leroux, M. Schlosser, Angew. Chem. 2002, 114, 4447-4450
32. Angew. Chem. Int. Ed. 2002, 41, 4272-4274
33. W. Lin, I. Sapountzis, P. Knochel, Angew. Chem. 2005, 117, 4330-4333
34. Angew. Chem. Int. Ed. 2005, 44, 4258-4261
35. I. Larrosa, M. I. D. Silva, P. M. Gõmez, P. Hannen, E. Ko, S. R. Lenger, S. R. Linke, A. J. P. White, D. Wilton, A. G. M. Barrett, J. Am. Chem. Soc. 2006, 128, 14042-14043
36. D. Soorukram, T. Qu, A. G. M. Barrett, Org. Lett. 2008, 10, 3833-3835.
37. H. Yoshida, E. Shirakawa, Y. Honda, T. Hiyama, Angew. Chem. 2002, 114, 3381-3383
38. Angew. Chem. Int. Ed. 2002, 41, 3247-3249
39. H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, Angew. Chem. 2004, 116, 4025-4028
40. Angew. Chem. Int. Ed. 2004, 43, 3935-3938
41. Z. Liu, R. C. Larock, J. Am. Chem. Soc. 2005, 127, 13112-13113
42. C. D. Gilmore, K. M. Allan, B. M. Stoltz, J. Am. Chem. Soc. 2008, 130, 1558-1559.
43. Bromoalkynylation of benzyne was reported by insertion of benzyne into CuBr and subsequent alkynylation of the resulting aryl copper species with bromoalkynes; see:, T. Morishita, H. Yoshida, J. Ohshita, Chem. Commun. 2010, 46, 640-642.
44. Generation of benzyne by halogen-lithium exchange of lithiated allyltrimethylsilane with 2-iodophenyl triflate has been reported; see:, A. Ganta, T. S. Snowden, Org. Lett. 2008, 10, 5103-5106.
45. P. H.-Y. Cheong, R. S. Paton, S. M. Bronner, G.-Y. Im, N. K. Garg, K. N. Houk, J. Am. Chem. Soc. 2010, 132, 1267-1269
46. G.-Y. Im, S. M. Bronner, A. E. Goetz, R. S. Paton, P. H.-Y. Cheong, K. N. Houk, N. K. Garg, J. Am. Chem. Soc. 2010, 132, 17933-17944.
47. We recently developed a one-pot dual cycloaddition of a benzdiyne equivalent; see:, T. Arisawa, T. Hamura, H. Uekusa, T. Matsumoto, K. Suzuki, Synlett 2008, 1179. See also Ref. [3c].
48. D. Seebach, M. Ertas, R. Locher, W. B. Schweizer, Helv. Chim. Acta 1985, 68, 264-281
49. M. Ertaş, D. Seebach, Helv. Chim. Acta 1985, 68, 961-969.
50. Lithium enolate 27 was generated by reaction of the ketene silyl acetal, prepared from tert-butyl acetate, and MeLi. For related reactions, see:, G. Stork, P. F. Hudrlik, J. Am. Chem. Soc. 1968, 90, 4464-4465.