Recent progress in the preparation of organoboron reagents via direct borylations

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 69, Issue 11, 2011, Pages 1212-1220

  Nishida, Mayumi ^a   Tagata, Tsuyoshi ^a  

^a Koei Chemical Company Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS;

BATCH REACTIONS; CONTINUOUS FLOW REACTION; CROSS COUPLING REACTIONS; DIRECT BORYLATION; ECONOMICAL METHODS; HETEROAROMATIC COMPOUNDS; HETEROGENEOUS CATALYST; SUZUKI-MIYAURA COUPLING;

CATALYSTS;

EID: 84855780942     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.69.1212     Document Type: Article

References (63)

1. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
2. (b) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
3. (c) Suzuki, A. Pure Appl. Chem. 1991, 63, 419.
4. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
5. (e) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
6. (f) Snieckus, V. Chem. Rev. 1990, 90, 879.
7. (g) Matteson, D. S. Tetrahedron 1989, 45, 1859.
8. (h) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 3437.
9. (i) Miyaura, N.; Yanagi, T.; Suzuki, A. Syn. Commun. 1981, 11, 513.
10. (j) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993.
11. (a) Manthy, M. K.; Truscott, S. G.; Truscott, J. W. J. Org Chem. 1990, 55, 4581.
12. (b) Bryant, J. A.; Helgeson, R. C.; Knobler C. B.; DeGrandpre, P. P.; Cram, D. J. J. Org Chem. 1990, 55, 4622.
13. (c) Helgeson, R. C.; Czech, B. P.; Chapoteau, E.; Gebauer, C. R.; Anaud. K.; Cram, D. J. J. Am. Chem. Soc 1989, 111, 6339.
14. (d) Yamamoto, Y.; Seco, T.; Němoto, H. J. Org Chem. 1989, 54, 4734.
15. (e) Schmidt, U.; Meyer, R.; Leitenberger, V.; Lieberknecht, A. Angew. Chem. 1989, 101, 946.
16. (f) Iihama, T.; Fu, J. M.; Bourguignon, M.; Snieckus, V. Synthesis 1989, 3, 184.
17. (g) Jung, M. E.; Young, Y H. Tetrahedron Lett. 1988, 29, 2517.
18. (a) Godard, A.; Marsais, E; Ple, N.; Trecourt, .R.; Turck, A. Heterocycles 1995, 2, 1055 and references therein,
19. (b) Queguiner, G.; Marsais, E; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1991, 52, 187 and references therein,
20. (c) Marsais, E; Godard, A.; Queguiner, G. J. Heterocycl. Chem. 1989, 26, 1589.
21. (a) Ishiyama T.; Murayama, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7908.
22. (b) Murata, M.; Watanabe S. Masuda, Y J. Org. Chem. 1997, 62, 6458.
23. (a) Iverson, C. N.; Smith III, M. R. J. Am. Chem. Soc 1999, 121, 7696.
24. (b) Cho, J.-Y.; Iverson, C. R.; Smith III, M. R. J. Am. Chem. Soc 2000, 122, 12868.
25. (c) Tse, M. K.; Cho, J.-Y.; Smith III, M. R. Org Lett. 2001, 3, 2831.
26. (d) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka Jr., R. E.; Smith III, M. R. Science 2002, 295, 305.
27. (e) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. E Science 2000, 287, 1995.
28. (f) Chen, H.; Schlecht, S.; Semple, T C.; Hartwig, J. E Angew. Chem. Int. Ed 1999, 38, 3391 .
29. (g) Shimada, S.; Batsanov, A. S.; Hward, J. A. K.; Marder, T B. Angew. Chem. Int. Ed 2001, 40, 2168.
30. (h) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3 and references therein,
31. (i) Ishiyama, T.; Miyaura, N. Chem. Rec 2004, 3, 271 and references therein,
32. (j) Ishiyama, T.; Takagi, J.; Hartwig, J. E; Miyaura, N. Angew. Chem. Int. Ed 2002, 16, 3056.
33. Boiler, T M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, R.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263.
34. Ishiyama, T.; Miyaura, N. Pure Appl. Chem. 2006, 78, 1369.
35. Tagata, T.; Nishida, M. Adv. Synth. Catal. 2004, 346, 1655.
36. Tagata, T.; Nishida, M.; Nishida, A. Tetrahedron Lett. 2009, 50, 6176.
37. Tagata, T.; Nishida, M.; Nishida, A. Adv. Synth. Catal. 2010, 352, 1662.
38. Takagi, J.; Sato, K.; Hartwig, J. E; Ishiyama, T.; Miyaura, R Tetrahedron Lett. 2002, 43, 5649.
39. Okabe, T.; Tanaka, H. Shokubai. 2008, 50 (1), 350.
40. (a) Zhu, Y H.; Yan, K. C.; Luo, J. Z.; Hwei, C. S.; Hon, Y C.; Emi, A.; Zhenshun, S.; Winata, M.; Hosmane, R S.; Maguire, J. A. J. Organomet. Chem. 2007, 692, 4244.
41. (b) Zhu, Y H.; Koh, C.; Ang, T. P.; Emi, A.; Monalisa, W; Loo, K. J. L.; Hosmane, R S.; Maguire, J. A. lnorg. Chem. 2008, 47, 5756.
42. Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131, 5058.
43. 7a, 7b and 7c are commercially available and are used as ligands for dye-sensitized solar cells, as electro-luminescent materials and as catalysts for polymers, see; (a) Wei, H.; Du, Y.; Kang, J. Z.; Xu, G. B.; Wang, E. K. Chin. J. Chem. 2007, 25, 159.
44. (b) Chen, C. Y.; Wu, S. J.; Wu, C. G.; Chen, J. G.; Ho, K. C. Angew. Chem. Int. Ed. 2006, 45, 5822.
45. Kuang, D.; Klein, C.; Snaith, H. J.; Moser, J. E.; HumphryBaker, R.; Comte, P.; Zakeeruddin, S. M.; Graetzel, M. Nano Lett. 2006, 6, 769.
46. (d) Min, D.; Yoon, S. S.; Lee, S. W lnorg. Chem. Commun. 2002, 5, 143.
47. 7b is available in industrial quantities from Koei Chemical Co, Ltd. It is prepared by the coupling reaction of 2-chloropyridine-4-carboxylic acid in the presence of Pd/C, hydrazine and base. See; Shimada, M. JP 2006240997.
48. According to a report by Miyaura, iridium complex prepared with 3,3'-dimethyl-2,2'-bipyridine as a ligand, which has a twist conformation between the two pyridyl units, is less active than 4,4'-dimethyl2,2'-bipyridine because the planarity of the bipyridine ring is important for the activity of the catalyst. See; Ishiyama, T.; Miyaura, N. Pure Appl. Chem. 2006, 78, 1369.
49. (a) Ruta, M.; Laurenczy, G.; Dyson, P. J.; Kiwi-Minsker, L. J. Phys. Chem. C 2008, 112, 17814.
50. (b) Burguete, M. I.; Erythropel, H.; Garcia-Verdugo, E.; Luis, S. V.; Sans, V. Green Chem. 2008, 10, 401.
51. (c) Sahoo, H. R.; Kralj, J. G.; Jensen, K. F. Angew. Chem. Int. Ed 2007, 46, 5704.
52. (d) Nikibin, R.; Ladlow, M.; Ley, S. V. Org Process Res. Dev. 2007, 11, 458.
53. (e) Hornung, C. H.; Mackley, M. R.; Baxendale, I. R.; Ley, S. V. Org. Process Res Dev. 2007, 11, 399.
54. (f) Desai, B.; Kappe, C. O. J. Comb. Chem. 2005, 7, 641.
55. (g) Bagley, M. G.; Jenkins, R. L.; Lubinu, M. C.; Mason, G.; Wood, R. J. Org Chem. 2005, 70, 7003.
56. (h) Phan, N. T. S.; Brown, D. H.; Styring, P. Green Chem. 2004, 6, 526.
57. (i) Pennemann, H.; Watts, P.; Haswell, S. J.; Hessel, V.; Lowe, H. Org Process Res. Dev. 2004, 8, 422.
58. (j) Haswell, S. J.; Watts, P. Green Chem. 2003, 5, 240.
59. (k) Ueno, M.; Hisamoto, H.; Kitamori, T.; Kobayashi, S. Chem. Commun. 2003, 936.
60. (l) Kirschning, A.; Altwicker, G.; Dränger, G.; Härders, J.; Hoffmann, R.; Hoffmann, U.; Schönfeld, H.; Solodenko, W.; Kunz, U. Angew. Chem. Int. Ed 2001, 40, 3995.
61. (m) Haswell, S. J.; Middleton, R. J.; Sullivan, B. O.; Skelton, V.; Watts, P.; Styring, P. Chem. Commun. 2001, 391.
62. (n) Khadilkar, B. M.; Madyar, V. R. Org. Process Res. Dev. 2001, 5, 452.
63. Baxendale, I. R.; Ley, S. V.; Mansfield, A. C.; Smith, C. D. Angew. Chem. Int. Ed 2009, 48, 4017.