A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

Angewandte Chemie - International Edition

Volumn 49, Issue 46, 2010, Pages 8729-8732

  Dudnik, Alexander S ^a   Chernyak, Natalia ^a   Huang, Chunhui ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

benzynes; C H activation; halogenation; palladium; siloles

Indexed keywords

ARYL IODIDES; BENZYNES; BUILDING BLOCKES; C-H ACTIVATION; EFFICIENT STRATEGY; HALOARENES; PYRIDYL; SILOLES; SYNTHONS;

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CATALYSIS; PALLADIUM; SILANES;

HALOGENATION;

BENZENE DERIVATIVE; BENZYNE; IODIDE; PALLADIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; HALOGENATION; SYNTHESIS;

BENZENE DERIVATIVES; CATALYSIS; HALOGENATION; IODIDES; PALLADIUM; SILANES;

EID: 78149454610     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004426     Document Type: Article

References (60)

1. For selected examples on importance of ambiphilic synthons, see
2. A. K. Yudin, R. Hili, Chem. Eur. J. 2007, 13, 6538
3. D. Tejedor, G. Méndez-Abt, J. González-Platas, M. A. Ramírez, F. García-Tellado, Chem. Commun. 2009, 2368
4. T. B. Samarakoon, M. Y. Hur, R. D. Kurtz, P. R. Hanson, Org. Lett. 2010, 12, 2182
5. E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2007, 129, 6716, and references therein.
6. For a review on directed ortho-metalation, see
7. V. Snieckus, Chem. Rev. 1990, 90, 879; for recent examples of employment of DOM group in cross-coupling reactions, see
8. K. W. Quasdorf, M. Riener, K. V. Petrova, N. K. Garg, J. Am. Chem. Soc. 2009, 131, 17748
9. A. Antoft-Finch, T. Blackburn, V. Snieckus, J. Am. Chem. Soc. 2009, 131, 17750.
10. N. Chernyak, A. S. Dudnik, C. Huang, V. Gevorgyan, J. Am. Chem. Soc. 2010, 132, 8270.
11. For selected recent reviews on transition-metal-catalyzed C-H activation of arenes, see
12. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
13. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
14. Angew. Chem. Int. Ed. 2009, 48, 5094
15. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
16. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173
17. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
18. Angew. Chem. Int. Ed. 2009, 48, 9792
19. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
20. For employment of pyridyldimethylsilyl directing group in Heck arylations, see
21. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2000, 122, 12013
22. K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; for employment of dimethylhydrosilyl directing group in iridium-catalyzed C-H borylations, see
23. D. W. Robbins, T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 4068
24. T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 7534.
25. For review on cross-coupling reactions of pivalates, see:, L. J. Gooßen, K. Gooßen, C. Stanciu, Angew. Chem. 2009, 121, 3621
26. Angew. Chem. Int. Ed. 2009, 48, 3569.
27. For representative examples of palladium-catalyzed directed C-H halogenation of arenes, see
28. D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Tetrahedron 2006, 62, 11483
29. D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Org. Lett. 2006, 8, 2523
30. T.-S. Mei, R. Giri, N. Maugel, J.-Q. Yu, Angew. Chem. 2008, 120, 5293
31. Angew. Chem. Int. Ed. 2008, 47, 5215
32. D. C. Powers, T. Ritter, Nat. Chem. 2009, 1, 302
33. T.-S. Mei, D.-H. Wang, J.-Q. Yu, Org. Lett. 2010, 12, 3140
34. F. Kakiuchi, T. Kochi, H. Mutsutani, N. Kobayashi, S. Urano, M. Sato, S. Nishiyama, T. Tanabe, J. Am. Chem. Soc. 2009, 131, 11310
35. O. S. Andrienko, V. S. Goncharov, V. S. Raida, Russ. J. Org. Chem. 1996, 32, 79.
36. For an excellent example of ruthenium-catalyzed o-silylation of arenes using a removable boron-tethered directing group, see:, H. Ihara, M. Suginome, J. Am. Chem. Soc. 2009, 131, 7502.
37. A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, H. Yamamoto, Angew. Chem. 1999, 111, 3916
38. Angew. Chem. Int. Ed. 1999, 38, 3701
39. K. Itami, M. Mineno, T. Kamei, J.-I. Yoshida, Org. Lett. 2002, 4, 3635.
40. Recently, it was shown that boronic acids could be ortho-iodinated under FriedelCrafts reaction conditions. However, the reported method is limited to electron-rich substrates only, see:, R. M. Al-Zoubi, D. G. Hall, Org. Lett. 2010, 12, 2480.
41. K. Itami, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2003, 125, 14670
42. T. Kamei, K. Itami, J.-I. Yoshida, Adv. Synth. Catal. 2004, 346, 1824
43. Z. Zhao, V. Snieckus, Org. Lett. 2005, 7, 2523
44. M. Rottländer, N. Palmer, P. Knochel, Synlett 1996, 573.
45. For a review on C-B bond formation through a C-H activation, see:, I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890.
46. R. S. Brown, H. Slebocka-Tilk, J. M. Buschek, J. G. Ulan, J. Am. Chem. Soc. 1984, 106, 5979.
47. G. A. Molander, B. W. Katona, F. Machrouhi, J. Org. Chem. 2002, 67, 8416.
48. T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org. Lett. 2000, 2, 1729.
49. L. Ilies, H. Tsuji, E. Nakamura, Org. Lett. 2009, 11, 3966.
50. A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020.
51. S. Furukawa, J. Kobayashi, T. Kawashima, J. Am. Chem. Soc. 2009, 131, 14192.
52. For reviews, see
53. H. H. Wenk, M. Winkler, W. Sander, Angew. Chem. 2003, 115, 518
54. Angew. Chem. Int. Ed. 2003, 42, 502
55. H. Pellissier, M. Santelli, Tetrahedron 2003, 59, 701.
56. Our initial attempts on direct conversion of the o-iodo derivatives 2 into benzynes were unsuccessful.
57. For selected examples on employment of o-(trimethylsilyl)phenyliodonium triflates as precursors for the preparation of benzyne, see
58. S. Kitamura, M. Yamane, J. Chem. Soc. Chem. Commun. 1995, 983
59. T. Kitamura, M. Yamane, K. Inoue, M. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674.
60. M. Bielawski, D. Aili, B. Olofsson, J. Org. Chem. 2008, 73, 4602.