Transition Metal-Catalyzed Element-Boryl Additions to Unsaturated Organic Compounds

Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2)

Volumn 1, Issue , 2011, Pages 171-212

  Suginome, Michinori ^a   Ohmura, Toshimichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Borylation; Carboboration; Diboration; Element boryl addition; Silaboration; Transmetalative carboboration

Indexed keywords

EID: 84877621565     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527639328.ch3     Document Type: Chapter

References (143)

1. (a) Okinoshima, H., Yamamoto, K., and Kumada, M. (1972) J. Am. Chem. Soc., 94, 9263-9264
2. (b) Okinoshima, H., Yamamoto, K., and Kumada, M. (1975) J. Organomet. Chem., 86, C27-C30.
3. (c) Sakurai, H., Kamiyama, Y., and Nakadaira, Y. (1975) J. Am. Chem. Soc., 97, 931-932.
4. Review on the element-silyl additions: Suginome, M. and Ito, Y. (2000) Chem. Rev., 100, 3221-3256.
5. Männig, D. and Nöth, H. (1985) Angew. Chem., Int. Ed., 24, 878-879.
6. Ishiyama, T., Matsuda, N., Miyaura, N., and Suzuki, A. (1993) J. Am. Chem. Soc., 115, 11018-11019.
7. Reviews on the element-element s-bond additions: (a) Beletskaya, I. andMoberg, C. (1999) Chem. Rev., 99, 3435-3462.
8. (b) Beletskaya, I. and Moberg, C. (2006) Chem. Rev., 106, 2320-2354.
9. Ceron, P., Frey, A.F.J., Kerrigan, J., Parsons, T., Urry, G., and Schlesinger, H.I. (1959) J. Am. Chem. Soc., 81, 6368-6371.
10. Reviews on the B-B additions: (a)Marder, T.B. and Norman, N.C. (1998) Top. Catal., 63-73
11. (b) Ishiyama, T. and Miyaura, N. (2000) J. Organomet. Chem., 611, 392-402.
12. (c) Ishiyama, T. and Miyaura, N. (2004) Chem. Rec., 3, 271-280.
13. (d) Dembitsky, V.M., Abu Ali, H., and Srebnic, M. (2003) Appl. Organomet. Chem., 17, 327-345.
14. (e) Dembitsky, V.M., Abu Ali, H., and Srebnic, M. (2004) Adv. Organomet. Chem., 51, 193-250.
15. (a) Nöth, H. (1984) Z. Naturforsch., 39b, 1463-1466.
16. (b) Ishiyama, T., Murata, M., Ahiko, T., and Miyaura, N. (2000) Org. Synth., 77, 176-181.
17. Welch, C.N. and Shore, S.G. (1968) Inorg. Chem., 7, 225.
18. Ishiyama, T., Matsuda, N., Murata, M., Ozawa, F., Suzuki, A., and Miyaura, N. (1996) Organometallics, 15, 713-720.
19. Lesley, G., Nguyen, P., Taylor, N.J., Marder, T.B., Scott, A.J., Clegg, W., and Norman, N.C. (1996) Organometallics, 15, 5137-5154.
20. Mann, G., John, K.D., and Baker, R.T. (2000) Org. Lett., 2, 2105-2108.
21. Lillo, V., Mata, J., Ramírez, J., Peris, E., and Fernandez, E. (2006) Organometallics, 25, 5829-5831.
22. Thomas, R.L., Souza, F.E.S., and Marder, T.B. (2001) J. Chem. Soc., Dalton Trans., 1650-1656.
23. Ali, H.A., Quntar, A.E.A.A., Goldberg, I., and Srebnik, M. (2002) Organometallics, 21, 4533-4539.
24. Maderna, A., Pritzkow, H., and Siebert, W. (1996) Angew. Chem., Int. Ed. Engl., 35, 1501-1503.
25. Bluhm, M., Maderna, A., Pritzkow, H., Bethke, S., Gleiter, R., and Siebert, W. (1999) Eur. J. Inorg. Chem., 1693-1700.
26. Iverson, C.N. and Smith, M.R., III (1995) J. Am. Chem. Soc., 117, 4403-4404.
27. (a) Ishiyama, T., Yamamoto, M., and Miyaura, N. (1997) Chem. Commun., 689-690.
28. (b) Iverson, C.N. and Smith, M.R., III (1997) Organometallics, 16, 2757-2759.
29. (c) Carter, C.A.G., Vogels, C.M., Harrison, D.J., Gagnon, M.K.J., Norman, D.W., Langler, R.F., Baker, R.T., and Westcott, S.A. (2001) Organometallics, 20, 2130-2132.
30. (a) Baker, R.T., Nguyen, P., Marder, T.B., and Westcott, S.A. (1995) Angew. Chem., Int. Ed. Engl., 34, 1336-1338.
31. (b) Dai, C., Robins, E.G., Scott, A.J., Clegg, W., Yufit, D.S., Howard, J.A.K., and Marder, T.B. (1998) Chem. Commun., 1983-1984.
32. (c) Nguyen, P., Coapes, R.B., Woodward, A.D., Taylor, N.J., Burke, J.M., Howard, J.A.K., and Marder, T.B. (2002) J. Organomet. Chem., 652, 77-85.
33. (d) Morgan, J.B., Miller, S.P., and Morken, J.P. (2003) J. Am. Chem. Soc., 125, 8702-8703.
34. Lillo, V., Mas-Marzá, E., Segarra, A.M., Carbó, J.J., Bo, C., Peris, E., and Fernández, E. (2007) Chem. Commun., 3380-3382.
35. Lillo, V., Fructos, M.R., Ramírez, J., Braga, A.A.C., Maseras, F., Díaz-Requejo, M.M., Pérez, P.J., and Fernández, E. (2007) Chem. Eur. J., 13, 2614-2621.
36. Ramírez, J., Corberán, R., Sanaú, M., Peris, E., and Fernández, E. (2005) Chem. Commun., 3056-3058.
37. Ramírez, J., Sanaú, M., and Fernández, E. (2008) Angew. Chem., Int. Ed., 47, 5194-5197.
38. Coapes, R.B., Souza, F.E.S., Thomas, R.L., Hall, J.J., and Marder, T.B. (2003) Chem. Commun., 614-615.
39. (a) Marder, T.B., Norman, N.C., and Rice, C.R. (1998) Tetrahedron Lett., 39, 155-158.
40. (b) Mkhalid, I.A.I., Coapes, R.B., Edes, S.N., Coventry, D.N., Souza, F.E.S., Thomas, R.L., Hall, J.J., Bi, S.-W., Lin, Z., and Marder, T.B. (2008) Dalton Trans., 1055-1064.
41. (a) Miller, S.P., Morgan, J.B., Nepveux, V.F.J., and Morken, J.P. (2004) Org. Lett., 6, 131-133.
42. (b) Trudeau, S., Morgan, J.B., Shrestha, M., and Morken, J.P. (2005) J. Org. Chem., 70, 9538-9544.
43. (c) Ramírez, J., Segarra, A.M., and Fernández, E. (2005) Tetrahedron Asymmetry, 16, 1289-1294.
44. Kliman, L.T., Mlynarski, S.N., and Morken, J.P. (2009) J. Am. Chem. Soc., 131, 13210-13211.
45. Ishiyama, T., Kitano, T., and Miyaura, N. (1998) Tetrahedron Lett., 39, 2357-2360.
46. Yang, F.-Y. and Cheng, C.-H. (2001) J. Am. Chem. Soc., 123, 761-762.
47. (a) Pelz, N.F., Woodward, A.R., Burks, H.E., Sieber, J.D., and Morken, J.P. (2004) J. Am. Chem. Soc., 126, 16328-16329.
48. (b) Burks, H.E., Liu, S., and Morken, J.P. (2007) J. Am. Chem. Soc., 129, 8766-8773.
49. Wang, M., Cheng, L., and Wu, Z. (2008) Organometallics, 27, 6464-6471.
50. Ishiyama, T., Yamamoto, M., and Miyaura, N. (1996) Chem. Commun., 2073-2074.
51. Burks, H.E., Kliman, L.T., and Morken, J.P. (2009) J. Am. Chem. Soc., 131, 9134-9135.
52. Cho, H.Y. and Morken, J.P. (2008) J. Am. Chem. Soc., 130, 16140-16141.
53. (a) Morgan, J.B. and Morken, J.P. (2003) Org. Lett., 5, 2573-2575.
54. (b) Ballard, C.E. and Morken, J.P. (2004) Synthesis, 1321-1324.
55. (a) Lawson, Y.G., Lesley, M.J.G., Marder, T.B., Norman, N.C., and Rice, C.R. (1997) Chem. Commun., 2051-2052.
56. (b) Ali, H.A., Goldberg, I., and Srebnik, M. (2001) Organometallics, 20, 3962-3965.
57. (c) Bell, N.J., Cox, A.J., Cameron, N.R., Evans, J.S.O., Marder, T.B., Duin, M.A., Elsevier, C.J., Baucherel, X., Tulloch, A.A.D., and Tooze, R.P. (2004) Chem. Commun., 1854-1855.
58. (a) Takahashi, K., Ishiyama, T., and Miyaura, N. (2000) Chem. Lett., 982-983.
59. (b) Ito, H., Yamanaka, H., Tateiwa, J., and Hosomi, A. (2000) Tetrahedron Lett., 41, 6821-6825.
60. (c) Takahashi, K., Ishiyama, T., and Miyaura, N. (2001) J. Organomet. Chem., 625, 47-53.
61. (d) Mun, S., Lee, J.-E., and Yun, J. (2006) Org. Lett., 8, 4887-4889.
62. (e) Chea, H., Sim, H.-S., and Yun, J. (2009) Adv. Synth. Catal., 351, 855-858.
63. (f) Bonet, A., Lillo, V., Ramírez, J., Díaz-Requejo, M.M., and Fernández, E. (2009) Org. Biomol. Chem., 7, 1533-1535.
64. Kabalka, G.W., Das, B.C., and Das, S. (2002) Tetrahedron Lett., 43, 2323-2325.
65. Hirano, K., Yorimitsu, H., and Oshima, K. (2007) Org. Lett., 9, 5031-5033.
66. Lee, K., Zhugralin, A.R., and Hoveyda, A.H. (2009) J. Am. Chem. Soc., 131, 7253-7255.
67. (a) Lee, J.-E. and Yun, J. (2008) Angew. Chem., Int. Ed., 47, 145-147.
68. (b) Feng, X. and Yun, J. (2009) Chem. Commun., 6577-6579.
69. (c) Fleming, W.J., Müller-Bunz, H., Lillo, V., Fernández, E., andGuiry, P.J. (2009) Org. Biomol. Chem., 7, 2520-2524.
70. Shiomi, T., Adachi, T., Toribatake, K., Zhou, L., and Nishiyama, H. (2009) Chem. Commun., 5987-5989.
71. Ishiyama, T., Momota, S., and Miyaura, N. (1999) Synlett, 1790-1791.
72. Ali, H.A., Goldberg, I., Kaufmann, D., Burmeister, C., and Srebnik, M. (2002) Organometallics, 21, 1870-1876.
73. (a) Hata, T., Kitagawa, H., Masai, H., Kurahashi, T., Shimizu, M., and Hiyama, T. (2001) Angew. Chem., Int. Ed., 40, 790-792.
74. (b) Kurahashi, T., Hata, T., Masai, H., Kitagawa, H., Shimizu, M., and Hiyama, T. (2002) Tetrahedron, 58, 6381-6395.
75. (c) Shimizu, M., Schelper, M., Nagao, I., Shimono, K., Kurahashi, T., and Hiyama, T. (2006) Chem. Lett., 35, 1222-1223.
76. Ishiyama, T., Yamamoto, M., and Miyaura, N. (1996) Chem. Lett., 1117-1118.
77. Ballard, C.E. and Morken, J.P. (2004) Synthesis, 1321-1324.
78. Nozaki, K., Wakamatsu, K., Nonaka, T., Tückmantel, W., Oshima, K., and Utimoto, K. (1986) Tetrahedron Lett., 27, 2007-2010.
79. Buynak, J.D. and Geng, B. (1995) Organometallics, 14, 3112-3115.
80. (a) Suginome, M., Nakamura, H., and Ito, Y. (1996) Chem. Commun., 2777-2778.
81. (b) Suginome, M., Matsuda, T., Nakamura, H., and Ito, Y. (1999) Tetrahedron, 55, 8787-8800.
82. Ohmura, T. and Suginome, M. (2009) Bull. Chem. Soc. Jpn., 82, 29-49.
83. (a) Shimizu, M., Kitagawa, H., Kurahashi, T., and Hiyama, T. (2001) Angew. Chem., Int. Ed., 40, 4283-4286.
84. (b) Shimizu, M., Kurahashi, T., Kitagawa, H., and Hiyama, T. (2003) Org. Lett., 5, 225-227.
85. (c) Shimizu, M., Kitagawa, H., Kurahashi, T., Shimono, K., and Hiyama, T. (2003) J. Organomet. Chem., 686, 286-293.
86. (d) Murakami, M., Usui, I., Hasegawa, M., and Matsuda, T. (2005) J. Am. Chem. Soc., 127, 1366-1367.
87. (a) Suginome, M., Fukuda, T., Nakamura, H., and Ito, Y. (2000) Organometallics, 19, 719-721.
88. (b) Suginome, M., Fukuda, T., and Ito, Y. (2002) J. Organomet. Chem., 643-644, 508-511.
89. Suginome, M., Ohmura, T., Miyake, Y., Mitani, S., Ito, Y., and Murakami, M. (2003) J. Am. Chem. Soc., 125, 11174-11175.
90. Suginome, M., Matsuda, T., and Ito, Y. (2000) Organometallics, 19, 4647-4649.
91. Ohmura, T., Masuda, K., Furukawa, H., and Suginome, M. (2007) Organometallics, 26, 1291-1294.
92. Onozawa, S., Hatanka, Y., and Tanaka, M. (1997) Chem. Commun., 1229-1230.
93. Da Silva, J.C.A., Birot, M., Pillot, J.-P., and Pétraud, M. (2002) J. Organomet. Chem., 646, 179-190.
94. Suginome, M., Noguchi, H., Hasui, T., and Murakami, M. (2005) Bull. Chem. Soc. Jpn., 78, 323-326.
95. Ohmura, T., Masuda, K., and Suginome, M. (2008) J. Am. Chem. Soc., 130, 1526-1527.
96. Sagawa, T., Asano, Y., and Ozawa, F. (2002) Organometallics, 21, 5879-5886.
97. Ohmura, T., Oshima, K., and Suginome, M. (2008) Chem. Commun., 1416-1418.
98. Suginome, M., Matsuda, T., and Ito, Y. (1998) Organometallics, 17, 5233-5235.
99. Lüken, C. and Moberg, C. (2008) Org. Lett., 10, 2505-2508.
100. Suginome, M., Nakamura, H., and Ito, Y. (1997) Angew. Chem., Int. Ed., 36, 2516-2518.
101. Ohmura, T., Furukawa, H., and Suginome, M. (2006) J. Am. Chem. Soc., 128, 13366-13367.
102. Ohmura, T., Takasaki, Y., Furukawa, H., and Suginome, M. (2009) Angew. Chem., Int. Ed., 48, 2372-2375.
103. Suginome, M., Matsuda, T., Yoshimoto, T., and Ito, Y. (1999) Org. Lett., 1, 1567-1569.
104. Suginome, M., Nakamura, H., Matsuda, T., and Ito, Y. (1998) J. Am. Chem. Soc., 120, 4248-4249.
105. (a) Gerdin, M. and Moberg, C. (2005) Adv. Synth. Catal., 347, 749-753.
106. (b) Gerdin, M., Penhoat, M., Zalubovskis, R., Pétermann, C., and Moberg, C. (2008) J. Organomet. Chem., 693, 3519-3526.
107. (c) Durieux, G., Gerdin, M., Moberg, C., and Jutand, A. (2008) Eur. J. Inorg. Chem., 4236-4241.
108. (a) Suginome, M., Ohmori, Y., and Ito, Y. (1999) Synlett, 1567-1568.
109. (b) Suginome, M., Ohmori, Y., and Ito, Y. (2000) J. Organomet. Chem., 611, 403-413.
110. Onozawa, S., Hatanaka, Y., and Tanaka, M. (1999) Chem. Commun., 1863-1864.
111. Ohmura, T. and Suginome, M. (2006) Org. Lett., 8, 2503-2506.
112. Ohmura, T., Taniguchi, H., and Suginome, M. (2006) J. Am. Chem. Soc., 128, 13682-13683.
113. Chang, K.-J., Rayabarapu, D.-K., Yang, F.- Y., and Cheng, C.-H. (2005) J. Am. Chem. Soc., 127, 126-131.
114. Abe, Y., Kuramoto, Y., Ehara, M., Nakatsuji, H., Suginome, M., Murakami, M., and Ito, Y. (2008) Organometallics, 27, 1736-1742.
115. Suginome, M., Matsuda, T., and Ito, Y. (2000) J. Am. Chem. Soc., 122, 11015-11016.
116. Pohlmann, T. and de Meijere, A. (2000) Org. Lett., 2, 3877-3879.
117. Ohmura, T., Taniguchi, H., Kondo, Y., and Suginome, M. (2007) J. Am. Chem. Soc., 129, 3518-3519.
118. Ohmura, T., Taniguchi, H., and Suginome, M. (2009) Org. Lett., 11, 2880-2883.
119. Suginome, M., Matsuda, T., Yoshimoto, T., and Ito, Y. (2002) Organometallics, 21, 1537-1539.
120. (a) Walter, C., Auer, G., and Oestreich, M. (2006) Angew. Chem., Int. Ed., 45, 5675-5677.
121. (b) Walter, C., and Oestreich, M. (2008) Angew. Chem., Int. Ed., 47, 3818-3820.
122. (c) Walter, C., Fröhlich, R., and Oestreich, M. (2009) Tetrahedron, 65, 5513-5520.
123. Suginome, M., Ohmori, Y., and Ito, Y. (2001) J. Am. Chem. Soc., 123, 4601-4602.
124. Suginome, M., Ohmori, Y., and Ito, Y. (2001) Chem. Commun., 1090-1091.
125. Mikhailov, B.M. andBubnov, Yu N. (1971) Tetrahedron Lett., 12, 2127-2130.
126. (a) Evers, E.C., Freitag, W.O., Kriner, W.A., and MacDiarmid, A.G. (1959) J. Am. Chem. Soc., 81, 5106-5108.
127. (b) Spielvogel, B.F., Bratton, R.F. and Moreland, C.G. (1972) J. Am. Chem. Soc., 94, 8597-8598.
128. (c) Bessler, V.E. and Goubeau, J.Z. (1967) Anorg. Allg. Chem., 352, 67-76.
129. (d) Meller, A., Maringgele, W., and Sicker, U. (1977) J. Organomet. Chem., 141, 249-255.
130. Suginome, M., Yamamoto, A., and Ito, Y. (2002) Chem. Commun., 1392-1393.
131. (a) Suginome, M., Yamamoto, A., and Murakami, M. (2003) J. Am. Chem. Soc., 125, 6358-6359.
132. (b) Ohmura, T., Awano, T., Suginome, M., Yorimitsu, H., and Oshima, K. (2008) Synlett, 423-427.
133. Yamamoto, A., Ikeda, Y., and Suginome, M. (2009) Tetrahedron Lett., 50, 3168-3170.
134. Suginome, M., Yamamoto, A., and Murakami, M. (2005) Angew. Chem., Int. Ed., 44, 2380-2382.
135. Suginome, M., Yamamoto, A., Sasaki, T., and Murakami, M. (2006) Organometallics, 25, 2911-2913.
136. Suginome, M., Shirakura, M., and Yamamoto, A. (2006) J. Am. Chem. Soc., 128, 14438-14439.
137. Yang, F.-Y., Wu, M.-Y., and Cheng, C.-H. (2000) J. Am. Chem. Soc., 122, 7122-7123.
138. Onozawa, S.-Y. and Tanaka, M. (2001) Organometallics, 20, 2956-2958.
139. Yamamoto, A. and Suginome, M. (2005) J. Am. Chem. Soc., 127, 15706-15707.
140. Daini, M., Yamamoto, A., and Suginome, M. (2008) J. Am. Chem. Soc., 130, 2918-2919.
141. Daini, M. and Suginome, M. (2008) Chem. Commun., 5224-5226.
142. Ishiyama, T., Nishijima, K., Miyaura, N., and Suzuki, A. (1993) J. Am. Chem. Soc., 115, 7219-7225.
143. Onozawa, S.-y., Hatanaka, Y., Sakakura, T., Shimada, S., and Tanaka, M. (1996) Organometallics, 15, 5450-5452.