Cyclic triolborate salts: Novel reagent for organic synthesis

Heterocycles

Volumn 85, Issue 4, 2012, Pages 799-819

  Yamamoto, Yasunori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84859771061     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/REV-12-728     Document Type: Article

References (114)

1. (a) N. Miyaura and Y. Yamamoto, 'Comprehensive Organometallic Chemistry III' Vol. 9, ed. by R. H. Crabtree and M. P. Mingos, Elsevier, 2007, pp. 146-244
2. (b) N. Miyaura, Bull. Chem. Soc. Jpn., 2008, 81, 1535
3. (c) D. G. Hall, 'Boronic Acids: Second, Completely Revised and Enlarged Edition,' Wiley-VCH, Weinheim, 2011.
4. R. W. Hoffmann and H.-J. Zeiss, Angew. Chem., Int. Ed. Engl., 1979, 18, 306; For review
5. J. W. Kennedy and D. G. Hall, 'Boronic acids, ' ed. by D. G. Hall, Wiley-VCH, Weinheim, 2005, pp. 241-277.
6. (a) N. Miyaura, K. Yamada, and A. Suzuki, Tetrahedron Lett., 1979, 36, 3437; For reviews
7. (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457
8. (c) N. Miyaura, 'Advances in Meta-Organic Chemistry,' Vol. 6, ed. by L. S. Liebeskind, JAI Press, London, 1998, pp. 187-243
9. (d) N. Miyaura, Topics in Current Chemistry, 2002, 219, 11
10. (e) A. Suzuki and H. C. Brown, 'Organic Syntheses via Boranes,' Vol. 3, Aldrich Chemical Co., Milwaukee, 2003
11. (f) N. Miyaura, 'Metal-Catalyzed Cross-Coupling Reactions, Second, Completely Revised and Enlarged Edition,' Vol. 1, ed. by A. de Meijere and F. Diederich, Wiley-VCH, Weinheim, 2004, pp. 41-124
12. (g) A. Suzuki and Y. Yamamoto, Chem. Lett., 2011, 40, 894.
13. (a) D. M. T. Chan, K. L. Manaco, R.-P. Wang, and M. P. Winters, Tetrahedron Lett., 1998, 39, 2933
14. (b) D. A. Evans, J. L. Katz, and T. R. West, Tetrahedron Lett., 1998, 39, 2937
15. (c) P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, and A. Combs, Tetrahedron Lett., 1998, 39, 2941; For reviews
16. (d) S. V. Ley and A. W. Thomas, Angew. Chem., Int. Ed., 2003, 42, 5400
17. (e) D. M. T. Chan and P. Y. S. Lam, 'Boronic acids,' ed. by D. G. Hall, Wiley-VCH, Weinheim, 2005, pp. 205-240.
18. (a) M. Sakai, H. Hayashi, and N. Miyaura, Organometallics, 1997, 16, 4229; For reviews:
19. (b) K. Fagnou and M. Lautens, Chem. Rev., 2003, 103, 169
20. (c) T. Hayashi and K. Yamasaki, Chem. Rev., 2003, 103, 2829
21. (d) K. Yoshida and T. Hayashi, 'Modern Rhodium-Catalyzed Organic Reactions,' ed. by P. A. Evans, Wiley-VCH, 2005, pp. 55-78
22. (e) Y. Yamamoto, T. Nishikata, and N. Miyaura, J. Synth. Org. Chem. Jpn. (Engl. Ed.), 2006, 64, 1112
23. (f) Y. Yamamoto, T. Nishikata, and N. Miyaura, Pure and Appl. Chem., 2008, 80, 807
24. (g) N. Miyaura, Synlett, 2009, 2039
25. (h) G. Berthon-Gelloz and T. Hayashi, 'Boronic acids, Second, Completely Revised and Enlarged Edition,' ed. by D. G. Hall, Wiley-VCH, Weinheim, 2011, pp. 263-313.
26. (a) S. Darses and J.-P. Genêt, Eur. J. Org. Chem., 2003, 4313
27. (b) G. A. Molander and N. Ellis, Acc. Chem. Res., 2007, 40, 275
28. (c) H. A. Stefani, R. Cella, and S. Adriano, Tetrahedron, 2007, 63, 3623
29. (d) S. Darses and J.-P. Genêt, Chem. Rev., 2008, 108, 288
30. (e) G. A. Molander and B. Canturk, Chem. Rev., 2009, 48, 9240
31. (f) G. A. Molander and L. Jean-Gérard, 'Boronic acids, Second, Completely Revised and Enlarged Edition,' ed. by D. G. Hall, Wiley-VCH, Weinheim, 2011, pp. 507-550.
32. A. N. Camidge, V. H. M. Goddard, H. Gopee, N. L. Harrison, D. L. Hughes, C. J. Schubert, B. M. Sutton, G. L. Watts, and A. J. Witehead, Org. Lett., 2006, 8, 4071.
33. (a) K. L. Billingsley and S. L. Buchwald, Angew. Chem. Int. Ed., 2008, 47, 4695
34. (b) R. R. Mullens, Tetrahedron Lett., 2009, 50, 6783.
35. (a) J. A. Soderquist, K. Matos, and A. Rane, Tetrahedron Lett., 1995, 36, 2401
36. (b) A. Fürstner and G. Seidel, Tetrahedron, 1995, 51, 11165.
37. C. H. Oh and S. H. Jung, Tetrahedron Lett., 2000, 41, 8513.
38. (a) P. G. Ciattini, E. Morera, and G. Ortar, Tetrahedron Lett., 1992, 33, 4815
39. (b) N. A. Bumagin and V. V. Bykov, Tetrahedron, 1997, 53, 14437.
40. B. A. Haag, C, Sämann, A. Jana, and P. Knochel, Angew. Chem. Int. Ed., 2011, 50, 7290.
41. (a) Y. Yamamoto, M. Takizawa, X.-Q. Yu, and N. Miyaura, Angew. Chem. Int. Ed., 2008, 47, 928
42. (b) Y. Yamamoto, J. Sugai, M. Takizawa, and N. Miyaura, Org. Synth., 2011, 88, 79
43. (c) G.-Q. Li, S. Kiyomura, Y. Yamamoto, and N. Miyaura, Chem. Lett., 2011, 40, 702.
44. (a) Y. Yamamoto and N. Miyaura, Wako Junyaku Jiho, 2008, 76, 2
45. (b) Y. Yamamoto and N. Miyaura, Wako Organic Square, 2009, 27, 2
46. (c) Y. Yamamoto and N. Miyaura, Organometallic
47. (a) Y. Yamamoto, M. Takizawa, X.-Q. Yu, and N. Miyaura, Heterocycles, 2010, 80, 359
48. (b) G.-Q. Li, Y. Yamamoto, and N. Miyaura, Synlett, 2011, 1769
49. (c) G.-Q. Li, Y. Yamamoto, and N. Miyaura, Tetrahedron, 2011, 67, 6804.
50. (d) X.-Q. Yu, Y. Yamamoto, and N. Miyaura, Chem. Asian J., 2008, 3, 1517.
51. (a) X.-Q. Yu, Y. Yamamoto, and N. Miyaura, Synlett, 2009, 994
52. (b) X.-Q. Yu, T. Shirai, Y. Yamamoto, and N. Miyaura, Chem. Asian J., 2011, 6, 932
53. (c) Y. Yamamoto, Y. Takahashi, K. Kurihara, and N. Miyaura, Aust. J. Chem., 2011, 64, 1447.
54. (a) H. G. Kuivila, J. F. Reuwer, Jr., and J. A. Mangravite, Can. J. Chem., 1963, 41, 081
55. (b) H. G. Kuivila, J. F. Reuwer, Jr., and J. A. Mangravite, J. Am. Chem. Soc., 1964, 86, 2666
56. (c) R. D. Brown, A. S. Buchanan, and A. A. Humffray, Aust. J. Chem., 1965, 18, 1521
57. (d) F. C. Fischer and E. Havinga, Recl. Trav. Chim. Pays-Bas, 1974, 93, 21
58. (e) B. P. Roques, D. Florentin, and M. Callanquin, J. Heterocycl. Chem., 1975, 12, 195;
59. (f) D. Florentin, M. C. Fournié-Zaluski, M. Callanquin, and B. P. Roques, J. Heterocycl. Chem., 1976, 13, 1265
60. (g) S. Gronowitz, V. Bobŝik, and K. Lawitz, Chemica Scripta., 1984, 23, 120
61. (h) T. Watanabe, N. Miyaura, and A. Suzuki, Synlett, 1992, 207.
62. (a) E. Tyrrell and P. Brookes, Synthesis, 2003, 469
63. (b) L.-C. Campeau and K. Fagnou, Chem. Soc. Rev., 2007, 36, 1058.
64. (a) A. Bouillon, J.-C. Lancelot, J. Sopkova de Oliveira Santos, V. Collot, P. R. Bovy, and S. Rault, Tetrahedron, 2003, 59, 10043
65. (b) I. A. I. Mkhalid, D. N. Coventry, D. Albesa-Jove, A. S. Batsanov, J. A. K. Howard, R. N. Perutz, and T. B. Marder, Angew. Chem. Int. Ed., 2006, 45, 489
66. (c) J. Z. Deng, D. V. Paone, A. T. Ginnetti, H. Kurihara, S. D. Dreher, S. A. Weissman, S. R. Stauffer, and C. S. Burgey, Org. Lett., 2009, 11, 345
67. (d) D. X. Yang, S. L. Colletti, K. Wu, M. Song, G. Y. Li, and H. C. Shen, Org. Lett., 2009, 11, 381.
68. (a) P. B. Hodgson and F. H. Salingue, Tetrahedron Lett., 2004, 45, 685
69. (b) P. Gros, A. Doudouh, Y. Fort, Tetrahedron Lett., 2004, 45, 6239
70. (c) C. Gütz and A. Lützen, Synthesis, 2010, 85.
71. (a) B. T. O'Neill, D. Yohannes, M. W. Bundesmann, and E. P. Arnold, Org. Lett., 2000, 2, 4201
72. (b) L. Ackermann and H. K. Potukuchi, Synlett, 2009, 2852.
73. (a) D. M. Knapp, E. P. Gillis, and M. D. Burke, J. Am. Chem. Soc., 2009, 131, 6961
74. (b) G. R. Dick, D. M. Knapp, E. P. Gillis, and M. D. Burke, Org. Lett., 2010, 12, 2314.
75. (a) S. J. Rettig and J. Trotter, Can. J. Chem., 1977, 55, 3071
76. (b) M. K. Cyrański, A. Jezierska, P. Klimentowska, J. J. Panek, and A. Sporzyński, J. Phys. Org. Chem., 2008, 21, 472.
77. (a) A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, and S. Rault, Tetrahedron, 2002, 58, 2885
78. (b) A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, and S. Rault, Tetrahedron, 2002, 58, 3323
79. (c) A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, and S. Rault, Tetrahedron, 2002, 58, 4369
80. (d) H. Matondo, S. Souirti, and M. Baboulène, Synth. Commun., 2003, 33, 795
81. (e) C. L. Cioffi, W. T. Spencer, J. J. Richards, and R. J. Herr, J. Org. Chem., 2004, 69, 2210
82. (f) K. L. Billingsley, K. W. Anderson, and S. L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 3484
83. (g) N. Kudo, M. Perseghini, and G. C. Fu, Angew. Chem. Int. Ed., 2006, 45, 1282
84. (h) R. Kuwano and J.-Y. Yu, Heterocyles, 2007, 74, 1233
85. (i) X.-L. Fu, L.-L. Wu, H.-Y. Fu, H. Chen, and R.-X. Li, Eur. J. Org. Chem., 2009, 2051
86. (j) K. M. Clapham, A. S. Batsanov, M. R. Bryce, and B. Tarbit, Org. Biomol. Chem., 2009, 7, 2155.
87. (a) M. Terashima, H. Kakimi, M. Ishikura, and K. Kamata, Chem. Pharm. Bull., 1983, 31, 4573
88. (b) M. Ishikura, M. Kamada, and M. Terashima, Heterocycles, 1984, 22, 265
89. (c) M. Ishikura, M. Kameda, and M. Terashima, Synthesis, 1984, 936
90. (d) M. Ishikura, T. Mano, I. Oda, and M. Terashima, Heterocycles, 1984, 22, 2471
91. (e) M. Ishikura, M. Kameda, T. Ohta, and M. Terashima, Heterocycles, 1984, 22, 2475
92. (f) M. Ishikura, T. Ohta, and M. Terashima, Chem. Pharm. Bull., 1985, 33, 4755
93. (g) M. Ishikura, I. Oda. and M. Terashima, Heterocycles, 1985, 23, 2375
94. (h) M. Ishikura, I. Oda, and M. Terashima, Heterocyles, 1987, 26, 1603.
95. (a) E. Vazquez, I. W. Davies, and J. F. Payack, J. Org. Chem., 2002, 67, 7551
96. (b) N. Pagano, J. Maksimoska, H. Bregman, D. S. Williams, R. D. Webster, F. Xue, and E. Meggers, Org. Biomol. Chem., 2007, 5, 1218
97. (c) T. Kinzel, Y. Zhang, and S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 14073
98. (d) M. Ishikura, Heterocycles, 2011, 83, 247.
99. K. Billingsley and S. L. Buchwald, J. Am. Chem. Soc., 2007, 129, 3358.
100. C. A. Fleckenstein and H. Plenio, J. Org. Chem., 2008, 73, 3236.
101. (a) N. Primas, A. Bouillon, J.-C. Lancelot, H. El-Kashef, and S. Rault, Tetrahedron, 2009, 65, 5739
102. (b) N. Primas, A. Bouillon, J.-C. Lancelot, and S. Rault, Tetrahedron, 2009, 65, 6348
103. (c) A. Thakur, K. Zhang, and J. Louie, Chem. Commun., 2012, 48, 203.
104. (a) G. A. Molander and B. Biolatto, J. Org. Chem., 2003, 68, 4302
105. (b) G. A. Molander, B. Canturk, and L. E. Kennedy, J. Org. Chem., 2009, 74, 973.
106. K. M. Clapham, A. S. Batsanov, R. D. R. Geenwood, M. R. Bryee, A. E. Smith, and B. Tarbit, J. Org. Chem., 2008, 73, 2176.
107. N. Henry, C. Enguehard-Gueiffier, I. Thery, and A. Gueiffier, Eur. J. Org. Chem., 2008, 4824.
108. A. C. Spivey, L. Shukla, and J. F. Hayler, Org. Lett., 2007, 9, 891.
109. (a) M. Pucheault, S. Darses, and J.-P. Genêt, Eur. J. Org. Chem., 2002, 3552
110. (b) K. Yoshida and T. Hayashi, Heterocycles, 2003, 59, 605.
111. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 1998, 120, 5579.
112. T. Itoh, T. Mase, T. Nishikata, T. Iyama, H. Tachikawa, Y. Kobayashi, Y. Yamamoto, and N. Miyaura, Tetrahedron, 2006, 62, 9610.
113. (a) Y. Yamamoto, K. Kurihara, N. Sugishita, K. Ohshita, D. Piao, and N. Miyaura, Chem. Lett., 2005, 34, 1224
114. (b) K. Kurihara, N. Sugishita, K. Ohshita, D.-G. Piao, Y. Yamamoto, and N. Miyaura, J. Organomet. Chem., 2007, 692, 428.