Anthranilamide: A simple, removable ortho -directing modifier for arylboronic acids serving also as a protecting group in cross-coupling Reactions

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2662-2665

  Ihara, Hideki ^a   Koyanagi, Masashi ^a   Suginome, Michinori ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79956073077     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200764g     Document Type: Article

References (46)

1. Hall, D. G. In Boronic Acids; Hall, D. G. Ed.; Wiley: Weinheim, 2005; p 1.
2. Iverson, C. N.; Smith, M. R., III J. Am. Chem. Soc. 1999, 121, 7696
3. Cho, J.-Y.; Iverson, C. N.; Smith, M. R., III J. Am. Chem. Soc. 2000, 122, 12868
4. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995
5. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168
6. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390
7. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305 Review: Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
8. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508
9. Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458
10. Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164
11. Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001
12. Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359
13. Zzhu, W.; Ma, D. Org. Lett. 2006, 8, 261
14. Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350
15. Use of a chiral diol for protection of a boronyl group: Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 2000, 65, 9194 Use of trfluoroborate for protection: Molander, G.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
16. Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 758
17. Noguchi, H.; Shioda, T.; Chou, C.-M.; Suginome, M. Org. Lett. 2008, 10, 377
18. Iwadate, N.; Suginome, M. J. Organomet. Chem. 2009, 694, 1713
19. Iwadate, N.; Suginome, M. Org. Lett. 2009, 11, 1899
20. Iwadate, N.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 2548
21. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716
22. Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466
23. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 14084
24. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961
25. Ishikawa, S.; Manabe, K. Chem. Lett. 2006, 35, 164
26. Ishikawa, S.; Manabe, K. Chem. Commun. 2006, 2589
27. Ishikawa, S.; Manabe, K. Chem. Lett. 2007, 36, 1302
28. Ishikawa, S.; Manabe, K. Tetrahedron 2010, 66, 297
29. Short reviews on iterative Suzuki-Miyaura coupling: Manabe, K.; Ishikawa, S. Chem. Commun. 2008, 3829
30. Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565
31. Wang, C.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 5240
32. For ortho -directed C-H silylation, see: Williams, N. A.; Uchimaru, Y.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1995, 1129
33. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 422
34. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Hayamizu, T.; Chatani, N.; Murai, S. Chem. Lett. 2002, 396
35. Kakiuchi, F.; Matsumoto, M.; Tsuchiya, K.; Igi, K.; Hayamizu, T.; Chatani, N.; Murai, S. J. Organomet. Chem. 2003, 686, 134
36. Tobisu, M.; Ano, Y.; Chatani, N. Chem. Asian J. 2008, 3, 1585
37. For representative C-H silylations without using directing groups, see: Klare, H. F. T.; Oestreich, M.; Ito, J.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312 and reference therein
38. Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502
39. For directed metalation (stoichiometric), see: Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306
40. Snieckus, V. Chem. Rev. 1990, 90, 879-933
41. Antoft-Finch, A.; Blackburn, T.; Snieckus, V. J. Am. Chem. Soc. 2009, 131, 17750 and references therein
42. For directed catalytic ortho -C-H functionalization, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, N.; Chatani, N. Nature 1993, 366, 529 For earlier pioneering work, see: Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728 Reviews: Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
43. Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005.
44. Chissick, S. S.; Dewar, M. J. S.; Maitlis, P. M. J. Am. Chem. Soc. 1959, 81, 6329
45. Chissick, S. S.; Dewar, M. J. S.; Maitlis, P. M. J. Am. Chem. Soc. 1961, 83, 2708
46. Non-directed, Ir-catalyzed silylation of thiophenes has been reported. Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508