Vinylic C-H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an iridium(I)-dtbpy complex

Chemistry - An Asian Journal

Volumn 3, Issue 12, 2008, Pages 2082-2090

  Kikuchi, Takao ^a   Takagi, Jun ^a   Isou, Hironori ^a   Ishiyama, Tatsuo ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Boron; C H activation; Cross coupling; Iridium; Regioselectivity

Indexed keywords

BORON DERIVATIVE; IRIDIUM; ORGANOMETALLIC COMPOUND; VINYL DERIVATIVE; VINYL ETHER;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; IRIDIUM; ORGANOMETALLIC COMPOUNDS; VINYL COMPOUNDS;

EID: 57349158588     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800157     Document Type: Article

References (109)

1. a) D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995;
2. b) D. G. Hall, Boronic Acids, Wiley-VCH, Weinheim, 2005;
3. c) N. Miyaura, Y. Yamamoto in Comprehensive Organometallic Chemistry III, Vol. 9 (Eds.: R. H. Crabtree, D. M. P. Mingo) Elsevier, Amsterdam, 2007, pp. 145-244.
4. a) A. N. Nesmeyanov, R. A. Sokolik, Methods of Elemento-Organic Chemistry, Vol. 1, North-Holland, Amsterdam, 1967;
5. b) A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988.
6. a) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508;
7. b) T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, Tetrahedron Lett. 1997, 38, 3447;
8. c) For reviews, see:T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392 ()();
9. d) T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271.
10. a) M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458;
11. b) M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164;
12. c) M. Murata, T. Oyama, S. Watanabe, Y. Masuda, Synthesis 2000, 778;
13. d) M. Murata, S. Watanabe, Y. Masuda, Tetrahedron Lett. 2000, 41, 5877.
14. a) H. Y. Chen, J. F. Hartwig, Angew. Chem. 1999, 111, 3597;
15. Angew. Chem. Int. Ed. 1999, 38, 3391;
16. b) H. Y. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
17. c) J. D. Lawrence, M. Takahashi, C. Bae, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 15334;
18. d) Y. Kondo, D. Carcfa-Cuadrado, J. F. Hartwig, N. K. Boaen, N. L. Wanger, M. A. Hillmyer, J. Am. Chem. Soc. 2002, 124, 1164.
19. S. Shimada, A. S. Batsanov, J. A. K. Howard, T. B. Marder, Angew. Chem. 2001, 113, 2226;
20. Angew. Chem. Int. Ed. 2001, 40, 2168.
21. a) C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1999, 121, 7696;
22. b) J.-Y. Cho, C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 2000, 122, 12868;
23. c) M. K. Tse, J.-Y. Cho, M. R. Smith III, Org. Lett. 2001, 3, 2831;
24. d) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr., M. R. Smith III, Science 2002, 295, 305.
25. a) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390;
26. b) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama, N. Miyaura, Tetrahedron Lett. 2002, 43, 5649;
27. c) T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem. 2002, 114, 3182;
28. Angew. Chem. Int. Ed. 2002, 41, 3056;
29. d) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig, N. Miyaura, Adv. Synth. Catal. 2003, 345, 1103;
30. e) T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2003, 680, 3;
31. T. M. Boller, J. M. Hapke, N. Anastasi, J. F. Hartwig, T. Ishiyama, N. Miyaura, J. Am. Chem. Soc. 2005, 127, 14263;
32. For a review, see: f) T. Ishiyama, N. Miyaura, Pure Appl. Chem. 2006, 78, 1369.
33. T. Ishiyama, Y. Nobuta, J. F. Hartwig, N. Miyaura, Chem. Commun. 2003, 2924.
34. I. A. I. Mkhalid, D. N. Coventry, D. Albesa-Jove, A. S. Batsanov, J. A. K. Howard, R. N. Perutz, T. B. Marder, Angew. Chem. 2006, 118, 503;
35. Angew. Chem. Int. Ed. 2006, 45, 489.
36. a) K. Kurotobi, M. Miyauchi, K. Takakura, T. Murafuji, Y. Sugihara, Eur. J. Org. Chem. 2003, 3663;
37. b) A. Datta, A. Köllhofer, H. Plenio, Chem. Commun. 2004, 1508;
38. c) D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder, R. N. Perutz, Chem. Commun. 2005, 2172;
39. d) H. Hata, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2005, 127, 8264.
40. a) T. Ishiyama, K. Sato, Y. Nishio, N. Miyaura, Angew. Chem. 2003, 115, 5504;
41. Angew. Chem. Int. Ed. 2003, 42, 5346;
42. b) T. Ishiyama, K. Sato, Y. Nishio, T. Saeki, N. Miyaura, Chem. Commun. 2005, 5065;
43. c) T. Saiki, Y. Nishio, T. Ishiyama, N. Miyaura, Organometallics 2006, 25, 6068.
44. a) M. Gerdin, C. Moberg, Org. Lett. 2006, 8, 2929;
45. b) S. J. Geier, E. E. Chapman, D. I. McIsaac, C. M. Vogels, A. Decken, S. A. Westcott, Inorg. Chem. Commun. 2006, 9, 788;
46. c) V. J. Olsson, K. J. Szabo, Angew. Chem. 2007, 119, 7015;
47. Angew. Chem. Int. Ed. 2007, 46, 6891;
48. d) A. Caballero, S. Sabo-Etienne, Organometallics 2007, 26, 1191;
49. e) K. C. Lam, Z. Lin, T. B. Marder, Organometallics 2007, 26, 3149;
50. f) I. A. I. Mkhalid, R. B. Coapes, S. N. Edes, D. N. Coventry, F. E. S. Souza, R. L. Thomas, J. J. Hall, S.-W. Bi, Z. Lin, T. B. Marder, Dalton Trans. 2008, 1055.
51. a) S. A. Wescott, N. J. Taylor, T. B. Marder, R. T. Baker, N. J. Jones, Chem. Commun. 1991, 304;
52. b) For reviews of catalyzed hydroboration, see: K. Burgess, M. J. Ohmeyer, Chem. Rev. 1991, 91, 1179;
53. c) I. Beletskaya, A. Pelter, Tetrahedron 1997, 53, 4957;
54. d) N. Miyaura, Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001.
55. a) R. T. Baker, J. C. Calabrese, S. A. Westcott, P. Nguyen, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 4367;
56. b) J. M. Brown, G. C. Lloyd-Jones, J. Am. Chem. Soc. 1994, 116, 866;
57. c) M. Murata, S. Watanabe, Y. Masuda, Tetrahedron Lett. 1999, 40, 2585;
58. d) M. Murata, K. Kawakita, T. Asana, S. Watanabe, Y. Masuda, Bull. Chem. Soc. Jpn. 2002, 75, 825;
59. e) S. A. Westcott, T. B. Marder, R. T. Baker, Organometallics 1993, 12, 975;
60. f) C. M. Vogels, P. G. Hayes, M. P. Sharver, S. A. Westcott, Chem. Commun. 2000, 51.
61. a) T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11018;
62. b) T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics 1996, 15, 713;
63. c) C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1995, 117, 4403;
64. d) C. N. Iverson, M. R. Smith III, Organometallics 1996, 15, 5155;
65. e) G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics 1996, 15, 5137;
66. f) For reviews, see:I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435, and references therein.
67. T. Kikuchi, J. Takagi, T. Ishiyama, N. Miyaura, Chem. Lett. 2008, 31, 664.
68. Handbook of C-H Transformation (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005, chap. III, pp. 97-276.
69. a) N. Miyaura in Metal-Catalyzed Cross-Coupling Reactions: Second, Completely Revised and Enlarged Edition (Eds.: A. Meijere, F. Diederich), Wiley-VCH, 2004, chap. 2;
70. b) Cross-Coupling Reactions-A Practical Guide (Ed.: N. Miyaura), Springer, Berlin, 2002;
71. c) A. Suzuki, H. C. Brown, Organic Syntheses Via Boranes, Vol. 3, Suzuki Coupling, Aldrich Chemical Co., Milwaukee, 2003.
72. a) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169;
73. b) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
74. c) Y. Yamamoto, T. Nishikata, N. Miyaura, J. Synth. Org. Chem. Jpn. 2006, 64, 1112.
75. V. Blanchot-Courtois, M. Fetizon, I. Hanna, Tetrahedron Lett. 1992, 33, 5061.
76. a) U. Hacksell, G. D. Daves Jr, Prog. Med. Chem. 1985, 22, 1;
77. b) K. Suzuki, T. Matsumoto in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2 (Ed.: G. Lukacs), Springer, Berlin, 1993, p. 353;
78. c) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Pergamon, Oxford, 1995;
79. d) M. H. D. Postema, C-Glycoside Synthesis, CRC, Florida, 1995.
80. M. A. Tius, J. Gomez-Galeno, X.-Q. Gu, J. H. Zaidi, J. Am. Chem. Soc. 1991, 113, 5775.
81. G. J. M. Irvine, J. Gerald, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper, G. R. Whittell, L. J. Wright, Chem. Rev. 1998, 98, 2685.
82. H. Tamura, H. Yamazaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 2003, 125, 16114.
83. P. Nguyen, H. P. Blom, S. A. Westcott, N. J. Taylor, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 9329.
84. C. Dai, G. Stringer, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Inorg. Chem. 1997, 36, 272.
85. S. Nomura, E. Kawanishi, K. Ueta, PCT WO 012326A1, 2005.
86. a) R. Uson, L. A. Oro, J. A. Cabeza, Inorg. Synth. 1985, 23, 126;
87. b) J. L. Herde, J. C. Lambert, C. V. Senoff, Inorg. Synth. 1974, 15, 18;
88. c) M. Green, T. A. Kuc, S. H. Taylor, J. Chem. Soc. A 1971, 2334.
89. a) T. Hayashi, M. Konishi, M. Kumada, Tetrahedron Lett. 1979, 20, 1871;
90. b) J. Chatt, F. G. Mann, J. Chem. Soc. 1939, 1622.
91. a) T. Ishiyama, M. Murata, T. A. Ahiko, N. Miyaura, Org. Synth. 2000, 77, 176;
92. b) C. E. Tucker, J. Davidson, P. Knochel, J. Org. Chem. 1992, 57, 3482.
93. a) F. H. Case, J. Am. Chem. Soc. 1946, 68, 2574;
94. b) P. Wehman, G. C. Dol, E. R. Moorman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1994, 13, 4856;
95. c) D. Wenkert, R. B. Woodward, J. Org. Chem. 1983, 48, 283;
96. d) C. Metallinos, F. B. Barrett, Y. Wang, S. Xu, N. J. Taylor, Tetrahedron 2006, 62, 11145.
97. a) W. E. Billups, G. A. Lee, B. E. Arney, Jr., K. H. Whitmire, J. Am. Chem. Soc. 1991, 113, 7980;
98. b) T. Breining, C. Schmidt, K. Polos, Synth. Commun. 1987, 17, 85;
99. c) M. A. Tius, J. G. Galeno, J. H. Zaidi, Tetrahedron Lett. 1988, 29, 6909.
100. a) R. W. Murray, D. L. Shiang, M. Singh, J. Org. Chem. 1991, 56, 3677;
101. b) F. Cottet, L. Cottier, G. Descotes, Synthesis 1987, 497;
102. c) P. L. Menez, V. Fargeas, I. Berque, J. Poisson, J. Ardisson, J. Org. Chem. 1995, 60, 3592;
103. d) J. K. Crandall, A. C. Clark, J. Org. Chem. 1972, 37, 4236;
104. e) C. Schmit, J. B. Falmagne, J. Escudero, H. Vanlierde, L. Ghosez, Org. Synth. 1990, 69, 199.
105. a) S. Shuto, Y. Yahiro, S. Ichikawa, A. Matsuda, J. Org. Chem. 2000, 65, 5547;
106. b) J.-P. Lellouche, S. Koeller, J. Org. Chem. 2001, 66, 693;
107. c) K. H. Dötz, F. Otto, M. Nieger, J. Organomet. Chem. 2001, 621, 77;
108. d) Y. Mori, H. Hayashi, J. Org. Chem. 2001, 66, 8666;
109. e) S. Torii, T. Inokuchi, Y. Masatsugu, Bull. Chem. Soc. Jpn. 1985, 58, 3629.