Metal-Catalyzed Borylation of C-H and C-Halogen Bonds of Alkanes, Alkenes, and Arenes for the Synthesis of Boronic Esters

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

Volumn 1, Issue , 2011, Pages 135-169

  Ishiyama, Tatsuo ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Alkenyl halide; Allylboronate; Boronic ester; Dehydrogenative coupling; Heteroatom; Palladium

Indexed keywords

EID: 84863461356     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527639328.ch2     Document Type: Chapter

References (300)

1. Nesmeyanov, A.N. and Sokolik, R.A. (1967) Methods of Elemento-Organic Chemistry, vol. 1, North-Holland, Amsterdam.
2. Matteson, D.S. (1995) Stereodirected Synthesis with Organoboranes, Springer, Berlin.
3. Miyaura, N. (2005) Science of Synthesis, vols 6.1.7 and 6.1.26 (eds D.E. Kaufmann and D.S. Matteson), Georg Thieme Verlag, Stuttgart.
4. Ishiyama, T. and Miyaura, N. (2005) Chapter 2, in Boronic Acids (ed. D.G. Hall), Wiley-VCH Verlag GmbH, Weinheim.
5. Miyaura, N. and Yamamoto, Y. (2007) Comprehensive Organometallic Chemistry III, vol. 9 (eds R.H. Crabtree, D.M. Mingos, and P. Knochel), Elsevier, Amsterdam, pp. 145-244.
6. (a) Burgess, K. and Ohlmeyer, M.J. (1991) Chem. Rev., 91, 1179-1191
7. (b) Beletskaya, I. and Pelter, A. (1997) Tetrahedron, 53, 4957-5026.
8. Miyaura, N. (2001) Chapter 1, in Catalytic Heterofunctionalization (eds A. Togni and H. Grützmacher), Wiley-VCH Verlag GmbH, Weinheim.
9. (a) Reviews for catalyzed reactions of B-B compounds: Marder, T.B. and Norman, N.C. (1998) Top. Catal., 5, 63-73
10. (b) Irvine, G.J., Lesley, M.J.G., Marder, T.B., Norman, N.C., Rice, C.R., Robins, E.G., Roper, W.R., Whittell, G.R., and Wright, L.J. (1998) Chem. Rev., 98, 2685-2722.
11. (c) Beletskaya, I. and Moberg, C. (1999) Chem. Rev., 99, 3435-3462.
12. (d) Ishiyama, T. and Miyaura, N. (2000) J. Organomet. Chem., 611, 392-402.
13. (e) Ishiyama, T. and Miyaura, N. (2004) Chem. Rec., 3, 271-280.
14. (f) Miyaura, N. (2008) Bull. Chem. Soc. Jpn., 81, 1535-1553.
15. Ishiyama, T., Nishijima, K.-i., Miyaura, N., and Suzuki, A. (1993) J. Am. Chem. Soc., 115, 7219-7225.
16. Review for addition reactions of B-Si compounds: Suginome, M. and Ito, Y. (2000) Chem. Rev., 100, 3221-3256.
17. Suginome, M., Yamamoto, A., and Murakami, M. (2003) J. Am. Chem. Soc., 125, 6358-6359.
18. Review for addition reactions of B-Sn compounds: Han, L.-B. and Tanaka, M. (1999) Chem. Commun., 395-402.
19. (a) Reviews for borylation of RX with B-B or H-B compounds: Miyaura, N. (2002) Top. Curr. Chem., 219, 11-59.
20. (b) Miyaura, N. (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd edn, vol. 1 (eds A. Meijere and F. Diederich), Wiley-VCH, pp. 41-124 and Refs [3, 5, 7, 8f ].
21. (a) Reviews for borylation of RH with B-B or H-B compounds: Ishiyama, T. and Miyaura, N. (2003) J. Organomet. Chem., 680, 3-11.
22. (b) Ishiyama, T. and Miyaura, N. (2006) Pure and Appl. Chem., 78, 1369-1375.
23. (c) Mkhalid, I.A.I., Barnard, J.H., Marder, T.B., Murphy, J.M., and Hartwig, J.F. (2010) Chem. Rev., 110, 890-931.
24. (a) Ishiyama, T., Matsuda, N., Miyaura, N., and Suzuki, A. (1993) J. Am. Chem. Soc., 115, 11018-11019
25. (b) Ishiyama, T., Matsuda, N., Murata, M., Ozawa, F., Suzuki, A., and Miyaura, N. (1996) Organometallics, 15, 713-720.
26. (a) Iverson, C.N. and Smith, M.R., III (1995) J. Am. Chem. Soc., 117, 4403-4404.
27. (b) Iverson, C.N. and Smith, M.R., III (1996) Organometallics, 15, 5155-5165.
28. (a) Lesley, G., Nguyen, P., Taylor, N.J., Marder, T.B., Scott, A.J., Clegg, W., and Norman, N.C. (1996) Organometallics, 15, 5137-5154.
29. (b) Kerr, A., Norman, N.C., Orpen, A.G., Quayle, M.J., Rice, C.R., Timms, P.L., Whittll, G.R., and Marder, T.B. (1998) Chem. Commun., 319-320.
30. (a) Knorr, J.R. and Merola, J.S. (1990) Organometallics, 9, 3008-3010.
31. (b) The reported regioselectivities are opposite due to misprint: A private communication. Westcott, S.A., Taylor, N.J., Marder, T.B., Baker, R.T., Jones, N.J., and Calabrese, J.C. (1991) J. Chem. Soc., Chem. Commun., 304-305
32. (c) Baker, R.T., Calabrese, J.C., Westcott, S.A., Nguyen, P., andMarder, T.B. (1993) J. Am. Chem. Soc.
33. Dai, C., Stringer, G., Marder, T.B., Scott, A.J., Clegg, W., and Norman, N.C. (1997) Inorg. Chem., 36, 272-273.
34. (a) Baker, R.T., Calabrese, J.C., Westcott, S.A., Nguyen, P., and Marder, T.B. (1993) J. Am. Chem. Soc., 115, 4367-4368.
35. (b) Dai, C., Stringer, G., Marder, T.B., Baker, R.T., Scott, A.J., Clegg, W., and Norman, N.C. (1996) Can. J. Chem., 74, 2026-2031.
36. Nguyen, P., Blom, H.P., Westcott, S.A., Taylor, N.J., and Marder, T.B. (1993) J. Am. Chem. Soc., 115, 9329-9330.
37. (a) Ishiyama, T., Takagi, J., Ishida, K., Miyaura, N., Anastasi, N.R., and Hartwig, J.F. (2002) J. Am. Chem. Soc., 124, 390-391.
38. (b) Boller, T.M., Murphy, J.M., Hapke, M., Ishiyama, T., Miyaura, N., and Hartwig, J.F. (2005) J. Am. Chem. Soc., 127, 14263-14278.
39. (a) Murata, M., Watanabe, S., and Masuda, Y. (1999) Tetrahedron Lett., 40, 2585-2588.
40. (b) Murata, M., Kawakita, K., Asana, T., Watanabe, S., and Masuda, Y. (2002) Bull. Chem. Soc. Jpn., 75, 825-829.
41. (a) Westcott, S.A., Marder, T.B., and Baker, R.T. (1993) Organometallics, 12, 975-979.
42. (b) Vogels, C.M., Hayes, P.G., Shaver, M.P., and Westcott, S.A. (2000) Chem. Commun., 51-52.
43. (c) Mkhalid, I.A.I., Coapes, R.B., Edes, S.N., Coventry, D.N., Souza, F.E., Thomas, R.L., Hall, J.J., Bi, S.W., Lin, Z., and Marder, T.B. (2008) Dalton Trans., 22, 1055-1064.
44. Brown, J.M. and Lloyd-Jones, G.C. (1994) J. Am. Chem. Soc., 116, 866-878.
45. Ishiyama, T., Murata, M., and Miyaura, N. (1995) J. Org. Chem., 60, 7508-7510.
46. Ishiyama, T., Itoh, Y., Kitano, T., and Miyaura, N. (1997) Tetrahedron Lett., 38, 3447-3450.
47. (a) Takahashi, K., Ishiyama, T., and Miyaura, N. (2000) Chem. Lett., 982-983.
48. (b) Takahashi, K., Ishiyama, T., and Miyaura, N. (2001) J. Organomet. Chem., 625, 47-53.
49. (a) Cui, Q., Musaev, D.G., and Morokuma, K. (1997) Organometallics, 16, 1355-1364.
50. (b) Sakaki, S. and Kikuno, T. (1997) Inorg. Chem., 36, 226-229.
51. (c) Cui, Q., Musaev, D.G., and Morokuma, K. (1998) Organometallics, 17, 742-751.
52. (d) Lam, W.H. and Lin, Z.Y. (2003) Organometallics, 22, 473-480.
53. Tamura, H., Yamazaki, H., Sato, H., and Sakaki, S. (2003) J. Am. Chem. Soc., 125, 16114-16126.
54. (a) Murata, M., Watanabe, S., and Masuda, Y. (1997) J. Org. Chem., 62, 6458-6459.
55. (b) Murata, M., Oyama, T., Watanabe, S., and Masuda, Y. (2000) J. Org. Chem., 65, 164-168.
56. Olsson, V.J., Sebelius, S., Selander, N., and Szabó, K.J. (2006) J. Am. Chem. Soc., 128, 4588-4589.
57. Sebelius, S., Olsson, V.J., and Szabó, K.J. (2005) J. Am. Chem. Soc., 127, 10478-10479.
58. Sebelius, S., Olsson, V.J., Wallner, O.A., and Szabó, K.J. (2006) J. Am. Chem. Soc., 128, 8150-8151.
59. (a) Aspley, C.J. and Williams, J.A.G. (2001) New J. Chem., 25, 1136-1147
60. (b) Thompson, A.L.S., Kabalka, G.W., Akula, M.R., and Huffman, J.W. (2005) Synthesis, 547-550.
61. Nakamura, H., Fujiwara, M., and Yamamoto, Y. (1998) J. Org. Chem., 63, 7529-7530.
62. Huang, Y., Chen, D., and Qing, F.-L. (2005) Synlett, 1740-1742.
63. Rosen, B.M., Huang, C., and Percec V., (2008) Org. Lett., 10, 2597-2600.
64. Euzenat, L., Horhant, D., Ribourdouille, Y., Duriez, C., Alcaraz, G., and Vaultier, M. (2003) Chem. Commun., 2280-2281.
65. Iwadate, N. and Suginome, M. (2009) J. Organomet. Chem., 694, 1713-1717.
66. (a) Wang, Y.-C. and Georghiou, P.E. (2002) Org. Lett., 4, 2675-2678.
67. (b) Yu, S., Saenz, J., and Srirangam, J.K. (2002) J. Org. Chem., 67, 1699-1702.
68. (c) Zaidlewicz, M. and Wolan, A. (2002) J. Organomet. Chem., 657, 129-135.
69. (d) Becht, J.M., Meyer, O., and Helmchen, G. (2003) Synthesis, 2805-2810.
70. (e) Perttu, E.K., Arnold, M., and Iovine, P.M. (2005) Tetrahedron Lett., 46, 8753-8756.
71. (a) Malan, C. and Morin, C. (1998) J. Org. Chem., 63, 8019-8020.
72. (b) Yuen, A.K.L. and Hutton, C.A. (2005) Tetrahedron Lett., 46, 7899-7903.
73. Zhu, L., Duquette, J., and Zhang, M. (2003) J. Org. Chem., 68, 3729-3732.
74. Ishiyama, T., Ishida, K., and Miyaura, N. (2001) Tetrahedron, 57, 9813-9816.
75. Billingsley, L.L., Barder, T.E., and Buchwald, S.L. (2007) Angew. Chem., Int. Ed., 46, 5359-5363.
76. Fürstner, A. and Seidel, G. (2002) Org. Lett., 4, 541-543.
77. (a) Appukkuttan, P., Eycken, E.V., and Dehaen, W. (2003) Synlett, 1204-1206.
78. (b) Metten, B., Smet, M., Boens, N., and Dehaen, W. (2005) Synthesis, 1838-1844.
79. (a) Brimble, M.A. and Lai, M.Y.H. (2003) Org. Biomol. Chem., 1, 2084-2095.
80. (b) Skaff, O., Jolliffe, K.A., and Hutton, C.A. (2005) J. Org. Chem., 70, 7353-7363.
81. (c) Han, F.S., Higuchi, M., and Kurth, D.G. (2007) Org. Lett., 9, 559-562.
82. Willis, D.M. and Strongin, R.M. (2000) Tetrahedron Lett., 41, 8683-8686.
83. Ma, Y., Song, C., Jiang, W., Xue, G., Cannon, J.F., Wang, X., and Andrus, M.B. (2003) Org. Lett., 5, 4635-4638.
84. (a) Nicolaou, K.C., Rao, P.B., Hao, J., Reddy, M.V., Rassias, G., Huang, X., Chen, D.Y.-K., and Snyder, S.A. (2003) Angew. Chem., Int. Ed., 42, 1753-1758.
85. (b) Nicolaou, K.C., Hao, J., Reddy, M.V., Rao, P.B., Rassias, G., Snyder, S.A., Huang, X., Chen, D.Y.-K., Brenzovich, W.E., Giuseppone, N., Giannakakou, P., and O'Brate, A. (2004) J. Am. Chem. Soc., 126, 12897-12906.
86. (a) Bringmann, G., Rüdenauer, S., Götz, D.C.G., Gulder, T.M.A., and Reichert, M. (2006) Org. Lett., 8, 4743-4746.
87. (b) Aratani, N. and Osuka, A. (2008) Chem. Commun., 4067-4069.
88. Dietrich-Buchecker, C., Colasson, B., Jouvenot, D., and Sauvage, J.-P. (2005) Chem. Eur. J., 11, 4374-4386.
89. Abbott, B. and Thompson, P. (2003) Aust. J. Chem., 56, 1099-1106.
90. Araki, H., Katoh, T., and Inoue, M. (2006) Synlett, 555-558.
91. Read, M.W., Escobedo, J.O., Willis, D.M., Beck, P.A., and Strongin, R.M. (2000) Org. Lett., 2, 3201-3204.
92. (a) Elder, A.M. and Rich, D.H. (1999) Org. Lett., 1, 1443-1446.
93. (b) Decicco, C.P., Song, Y., and Evans, D.A., (2001) Org. Lett., 3, 1029-1032.
94. (c) Albrecht, B.K. and Williams, R.M. (2003) Org. Lett., 5, 197-200.
95. (d) Bois-Choussy, M., Cristau, P., and Zhu, J. (2003) Angew. Chem., Int. Ed., 42, 4238-4241.
96. (e) Inoue, M., Sakazaki, H., Furuyama, H., and Hirama, M. (2003) Angew. Chem., Int. Ed., 42, 2654-2657.
97. (f) Lin, S., Yang, Z.-Q., Kwok, B.H.B., Koldobskiy, M., Crews, C.M., and Danishefsky, S.J. (2004) J. Am. Chem. Soc., 126, 6347-6355.
98. (g) Gerstenberger, B.S. and Konopelski, J.P., (2005) J. Org. Chem., 70, 1467-1470.
99. (h) Roberts, T.C., Smith, P.A., Cirz, R.T., and Romesberg, F.E. (2007) J. Am. Chem. Soc., 129, 15830-15838.
100. Obst, U., Betschman, P., Lerner, C., Seiler, P., Diederich, F., Gramlich, V., Weber, L., Banner, D.W., and Schönholzer, P. (2000) Helv. Chim. Acta, 83, 855-1048.
101. Yasuda, S., Yorimitsu, H., and Oshima, K. (2008) Organometallics, 27, 4025-4027.
102. Piettre, S.R. and Baltzer, S. (1997) Tetrahedron Lett., 38, 1197-1200.
103. (a) Koizumi, Y., Seki, S., Acharya, A., Saeki, A., and Tagawa, S., (2004) Chem. Lett., 33, 1290-1291.
104. (b) Dudek, S.P., Pouderoijen, M., Abbel, R., Schenning, A.P.H.J., and Meijer, E.W. (2005) J. Am. Chem. Soc., 127, 11763-11768.
105. (c) Hiroki, K. and Kijima, M. (2005) Chem. Lett., 34, 942-943.
106. (d) Wong, W.W.H., Jones, D.J., Yan, C., Watkins, S.E., King, S., Haque, S.A., Wen, X., Ghiggino, K.P., and Holmes, A.B. (2009) Org. Lett., 11, 975-978.
107. (a) Zembower, D.E. and Zhang, H. (1998) J. Org. Chem., 63, 9300-9305.
108. (b) Nicolaou, K.C., Huang, X., Giuseppone, N., Rao, P.B., Bella, M., Reddy, M.V., and Snyder, S.A. (2001) Angew. Chem., Int. Ed., 40, 4705-4709
109. (c) Kaiser, M., Groll, M., Renner, C., Huber, R., and Moroder, L. (2002) Angew. Chem., Int. Ed., 41, 780-783.
110. (d) Kaiser, M., Siciliano, C., Assfalg-Machleidt, I., Groll, M., Milbradt, A.G., and Moroder, L. (2003) Org Lett., 5, 3435-3437.
111. (e) Yoburn, J.C. and Vranken, D.L.V. (2003) Org. Lett., 5, 2817-2820.
112. (f) Zheng, X., Meng, W.-D., and Qing, F.-L. (2004) Tetrahedron Lett., 45, 8083-8085.
113. (g) Nicolaou, K.C., Snyder, S.A., Giuseppone, N., Huang, X., Bella, M., Reddy, M.V., Rao, P.B., Koumbis, A.E., Giannakakou, P., and O'Brate, A. (2004) J. Am. Chem. Soc., 126, 10174-10182.
114. (h) Nicolaou, K.C., Snyder, S.A., Huang, X., Simonsen, K.B., Koumbis, A.E., and Bigot, A. (2004) J. Am. Chem. Soc., 126, 10162-10173.
115. (i) Davies, J.R., Kane, P.D., and Moody, C.J. (2005) J. Org. Chem., 70, 7305-7316.
116. (j) Lépine, R. and Zhu, J. (2005) Org. Lett., 7, 2981-2984.
117. (k) Shinohara, T., Deng, H., Snapper, M.L., and Hoveyda, A.H. (2005) J. Am. Chem. Soc., 127, 7334-7336.
118. (l) Jones, S.B., He, L., and Castle, S.L. (2006) Org. Lett., 8, 3757-3760.
119. (m) DiMauro, E.F. and Vitullo, J.R. (2006) J. Org. Chem., 71, 3959-3962.
120. (n) Jia, Y., Bois-Choussy, M., and Zhu, J. (2007) Org. Lett., 9, 2401-2404.
121. (o) Young, R.J., Borthwick, A.D., Brown, D., Burns-Kurtis, C.L., Campbell, M., Chan, C., Charbaut, M., Chung, C.W., Convery, M.A., Kelly, H.A., King, N.P., Kleanthous, S., Mason, A.M., Pateman, A.J., Patikis, A.N., Pinto, I.L., Pollard, D.R., Senger, S., Shah, G.P., Toomey, J.R., Watson, N.S., and Weston, H.E. (2008) Bioorg. Med. Chem. Lett., 18, 23-27.
122. (p) Lee, S.J., Gray, K.C., Paek, J.S., and Burke, M.D. (2008) J. Am. Chem. Soc., 130, 466-468.
123. (q) Bourdreux, Y., Nowaczyk, S., Billaud, C., Mallinger, A., Willis, C., Murr, M.D.-E., Toupet, L., Lion, C., Gall, T.L., and Mioskowski, C. (2008) J. Org. Chem., 73, 22-26
124. (r) Bringmann, G., Rüdenauer, S., Bruhn, T., Benson, L., and Brun, R. (2008) Tetrahedron, 64, 5563-5568.
125. (s) Lin, J., Gerstenberger, B.S., Stessman, N.Y.T., and Konopelski, J.P. (2008) Org. Lett., 10, 3969-3972.
126. (t) Michaux, J., Retailleau, P., and Campagne, J.-M. (2008) Synlett, 1532-1536.
127. (u) Nielsen, D.K., Nielsen, L.L., Jones, S.B., Toll, L., Asplund, M.C., and Castle, S.L. (2009) J. Org. Chem., 74, 1187-1199.
128. (a) Iovine, P.M., Kellett, M.A., Redmore, N.P., and Therien, M.J. (2000) J. Am. Chem. Soc., 122, 8717-8727.
129. (b) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc., 123, 2517-2524.
130. (c) Kurotobi, K., Tabata, H., Miyauchi, M., Murafuji, T., and Sugihara, Y. (2002) Synthesis, 1013-1016.
131. (d) Han, J.W., Castro, J.C., and Burgess, K. (2003) Tetrahedron Lett., 44, 9359-9362.
132. (e) Ni, W., Fang, H., Springsteen, G., and Wang, B. (2004) J. Org. Chem., 69, 1999-2007.
133. (f) Zheng, X., Mulcahy, M.E., Horinek, D., Galeotti, F., Magnera, T.F., and Michl, J. (2004) J. Am. Chem. Soc., 126, 4540-4542.
134. (g) Chang, M.C.Y., Pralle, A., Isacoff, E.Y., and Chang, C.J. (2004) J. Am. Chem. Soc., 126, 15392-15393.
135. (h) Bell, T.D.M., Jacob, J., Angeles-Izquierdo, M., Fron, E., Nolde, F., Hofkens, J., Müllen, K., and Schryver, F.C.D. (2005) Chem. Commun., 4973-4975.
136. (i) Miller, E.W., Albers, A.E., Pralle, A., Isacoff, E.Y., and Chang, C.J. (2005) J. Am. Chem. Soc., 127, 16652-16659.
137. (j) Wang, S., Hong, J.W., and Bazan, G.C., (2005) Org. Lett., 7, 1907-1910.
138. (k) Welter, S., Salluce, N., Benetti, A., Rot, N., Belser, P., Sonar, P., Grimsdale, A.C., Müllen, K., Lutz, M., Spek, A.L., and Cola, L.D. (2005) Inorg. Chem., 44, 4706-4718.
139. (l) Cheung, K.-M., Zhang, Q.-F., Chan, K.-W., Lam, M.H.W., Williams, I.D., and Leung, W.-H. (2005) J. Organomet. Chem., 690, 2913-2921.
140. (m) Thiemann, F., Piehler, T., Haase, D., Saak, W., and Lützen, A. (2005) Eur. J. Org. Chem., 1991-2001.
141. (n) Yuan, S.-C., Chen, H.-B., Zhang, Y., and Pei, J. (2006) Org. Lett., 8, 5701-5704.
142. (o) Albers, A.E., Okreglak, V.S., and Chang, C.J. (2006) J. Am. Chem. Soc., 128, 9640-9641.
143. (p) Kiehne, U., Bunzen, J., Staats, H., and Lützen, A. (2007) Synthesis, 1061-1069
144. (q) Yang, Y.J. and Nocera, D.G. (2007) J. Am. Chem. Soc., 129, 8192-8198.
145. (r) Jacobsen, M.F., Andersen, C.S., Knudsen, M.M., and Gothelf, K.V. (2007) Org. Lett., 9, 2851-2854.
146. (s) Bhayana, B. and Wilcox, C.S. (2007) Angew. Chem., Int. Ed., 46, 6833-6836.
147. (t) Fendt, L.-A., Fang, H., Plonska-Brzezinska, M.E., Zhang, S., Cheng, F., Braun, C., Echegoyen, L., and Diederich, F. (2007) Eur. J. Org. Chem., 4659-4673.
148. (u) Trokowski, R., Akine, S., and Nabeshima, T. (2008) Chem. Commun., 889-890.
149. (v) Noguchi, H., Shioda, T., Chou, C.-M., and Suginome, M. (2008) Org. Lett., 10, 377-380.
150. (w) Bolink, H.J., Santamaria, S.G., Sudhakar, S., Zhen, C., and Sellinger, A. (2008) Chem. Commun., 618-620.
151. (x) Su, S.-J., Tanaka, D., Li, Y.-J., Sasabe, H., Takeda, T., and Kido, J. (2008) Org. Lett., 10, 941-944.
152. (a) Deng, X. and Cai, C. (2003) Tetrahedron Lett., 44, 815-817.
153. (b) Chi, C., Im, C., Enkelmann, V., Ziegler, A., Lieser, G., and Wegner, G. (2005) Chem. Eur. J., 11, 6833-6845.
154. (c) Iyer, P.K. and Wang, S. (2006) Tetrahedron Lett., 47, 437-439.
155. (d) Jiang, Y., Lu, Y.-X., Cui, Y.-X., Zhou, Q.-F., Ma, Y., and Pei, J. (2007) Org. Lett., 9, 4539-4542.
156. (e) Chi, C., Mikhailovsky, A., and Bazan, G.C. (2007) J. Am. Chem. Soc., 129, 11134-11145.
157. (f) Pol, C.V.D., Bryce, M.R., Wielopolski, M., Atienza-Castellanos, C., Guldi, D.M., Filippone, S., and Martin, N. (2007) J. Org. Chem., 72, 6662-6671.
158. (g) Vives, G., Gonzalez, A., Jaud, J., Launay, J.-P., and Rapenne, G. (2007) Chem. Eur. J., 13, 5622-5631.
159. (h) Araki, H., Katoh, T., and Inoue, M. (2007) Tetrahedron Lett., 48, 3713-3717.
160. (i) Kulasi, A., Yi, H., and Iraqi, A. (2007) J. Polymer. Sci. A, 23, 5957-5967.
161. (j) Zhang, M., Yang, C., Mishra, A.K., Pisula, W., Zhou, G., Schmaltz, B., Baumgarten, M., and Müllen, K. (2007) Chem. Commun., 1704-1706.
162. (k) Liu, B. and Dishari, S.K. (2008) Chem. Eur. J., 14, 7366-7375.
163. (l) Figueira-Duarte, T.M., Simon, S.C., Wagner, M., Druzhinin, S.I., Zachariasse, K.A., and Müllen, K. (2008) Angew. Chem., Int. Ed., 47, 10175-10178.
164. (m) Fang, F.-C., Chu, C.-C., Huang, C.- H., Raffy, G., Guerzo, A.D., Wong, K.-T., and Bassani, D.M. (2008) Chem. Commun., 6369-6371.
165. (a) Broutin, P.-E., Ĉern̂a, I., Campaniello, M., Leroux, F., and Colobert, F. (2004) Org. Lett., 6, 4419-4422.
166. (b) Murata, M., Sambommatsu, T., Watanabe, S., and Masuda, Y. (2006) Synlett, 1867-1870.
167. Stadlwieser, J.F. and Dambaur, M.E. (2006) Helv. Chem. Acta, 89, 936-946.
168. (a) Baudoin, O., Guénard, D., and Guéritte, F. (2000) J. Org. Chem., 65, 9268-9271.
169. (b) Billingsley, K.L., Anderson, K.W., and Buchwald, S.L., (2006) Angew. Chem., Int. Ed., 45, 3484-3488.
170. (c) Billingsley, K.L. and Buchwald, S.L. (2007) J. Am. Chem. Soc., 129, 3358-3366.
171. (d) Billingsley, K.L. and Buchwald, S.L. (2008) J. Org. Chem., 73, 5589-5591.
172. Christophersen, C., Begtrup, M., Ebdrup, S., Petersen, H., and Vedsø, P. (2003) J. Org. Chem., 68, 9513-9516.
173. (a) Melaimi, M., Mathey, F., and Floch, P.L. (2001) J. Organomet. Chem., 640, 197-199.
174. (b) Melaimi, M., Thoumazet, C., Ricard, L., and Floch, P.L. (2004) J. Organomet. Chem., 689, 2988-2994.
175. (a) Zhu, W. andMa, D. (2006) Org. Lett., 8, 261-263.
176. (b) Kleeberg, C., Dang, L., Lin, Z., and Marder, T.B. (2009) Angew. Chem., Int. Ed., 48, 5350-5354.
177. Mentzel, U.V., Tanner, D., and Tønder, J.E. (2006) J. Org. Chem., 71, 5807-5810.
178. Gravett, E.C., Hilton, P.J., Jones, K., and Péron, J.M. (2003) Synlett, 253-255.
179. (a) Nakamura, H., Fujiwara, M., and Yamamoto, Y. (2000) Bull. Chem. Soc. Jpn., 73, 231-235.
180. (b) Combs, A.P., Zhu, W., Crawley, M.L., Glass, B., Polam, P., Sparks, R.B., Modi, D., Takvorian, A., McLaughlin, E., Yue, E.W., Wasserman, Z., Bower, M., Wei, M., Rupar, M., Ala, P.J., Reid, B.M., Ellis, D., Gonneville, L., Emm, T., Taylor, N., Yeleswaram, S., Li, Y., Wynn, R., Burn, T.C., Hollis, G., Liu, P.C.C., and Metcalf, B. (2006) J. Med. Chem., 49, 3774-3789.
181. (a) Wolan, A. and Zaidlwicz, M. (2003) Org. Biomol. Chem., 1, 3274-3276.
182. (b) Horn, J., Marsden, S.P., Nelson, A., House, D., and Weingarten, G.G. (2008) Org. Lett., 10, 4117-4120.
183. (a) Setsune, J., Toda, M., Watanabe, K., Panda, P.K., and Yoshida, T. (2006) Tetrahedron Lett., 47, 7541-7544.
184. (b) Pinkerton, D.M., Banwell, M.G., and Willis, A.C. (2007) Org. Lett., 9, 5127-5130.
185. Heinrich, M.R., Steglich, W., Banwell, M.G., and Kashman, Y. (2003) Tetrahedron, 59, 9239-9247.
186. (a) Chng, L.L., Chang, C.J., and Nocera, D.G. (2003) J. Org. Chem., 68, 4075-4078.
187. (b) Felber, B. and Diederich, F. (2005) Helv. Chim. Acta, 88, 120-153.
188. (c) Zhang, T.-G., Zhao, Y., Asselberghs, I., Persoons, A., Clays, K., and Therien, M.J. (2005) J. Am. Chem. Soc., 127, 9710-9720.
189. (d) Cheng, F., Zhang, S., Adronov, A., Echegoyen, L., and Diederich, F. (2006) Chem. Eur. J., 12, 6062-6070.
190. (e) Dahms, K. and Senge, M.O. (2008) Tetrahedron Lett., 49, 5397-5399.
191. (a) Baudoin, O., Décor, A., Cesario, M., and Guéritte, F. (2003) Synlett, 2009-2012.
192. (b) Joncour, A., Décor, A., Liu, J.-M., Dau, M.-E.T.H., and Baudoin, O. (2007) Chem. Eur. J., 13, 5450-5465.
193. Chan, J.M.W. and Swager, T.M. (2008) Tetrahedron Lett., 49, 4912-4914.
194. (a) Selected references: Murr, M.D.-E., Nowaczyk, S., Gall, T.L., Mioskowski, C., Amekraz, B., and Moulin, C. (2003) Angew. Chem., Int. Ed., 42, 1289-1293.
195. (b) Penhoat, M., Levacher, V., and Dupas, G. (2003) J. Org. Chem., 68, 9517-9520.
196. (c) Pla, D., Marchal, A., Olsen, C.A., Albericio, F., and Álvarez, M. (2005) J. Org. Chem., 70, 8231-8234.
197. (d) Casimiro-Garcia, A. and Schultz, A.G. (2006) Tetrahedron Lett., 47, 2739-2742.
198. (e) Babudri, F., Cardone, A., Gioffi, C.T., Farinola, G.M., Naso, F., and Ragni, R. (2006) Synthesis, 1325-1332.
199. (f) Altemöller, M., Podlech, J., and Fenske, D. (2006) Eur. J. Org. Chem., 1678-1684.
200. (g) Wipf, P. and Furegati, M. (2006) Org. Lett., 8, 1901-1904.
201. (h) Kasahara, T. and Kondo, Y. (2006) Chem. Commun., 891-893.
202. (i) Miller, W.D., Fray, A.H., Quatroche, J.T., and Sturgill, C.D. (2007) Org. Process Res. Dev., 11, 359-364.
203. (j) Liu, W., Buck, M., Chen, N., Shang, M., Taylor, N.J., Asoud, J., Wu, X., Hasinoff, B.B., and Dmitrienko, G.I. (2007) Org. Lett., 9, 2915-2918.
204. (k) Roach, S.L., Higuchi, R.I., Adams, M.E., Liu, Y., Karanewsky, D.S., Marschke, K.B., Mais, D.E., Miner, J.N., and Zhi, L. (2008) Bioorg. Med. Chem. Lett., 18, 3504-3508.
205. (l) Duong, H.A., Chua, S., Huleatt, P.B., and Chai, C.L.L. (2008) J. Org. Chem., 73, 9177-9180; (m) Morrison, M.D., Hanthorn, J.J., and Pratt, D.A. (2009) Org. Lett., 11, 1051-1054.
206. (m) Morrison, M.D., Hanthorn, J.J., and Pratt, D.A. (2009) Org. Lett., 11, 1051-1054.
207. (a) Selected references: Krámer, C.S., Zeitler, K., and Müller, T.J.J. (2001) Tetrahedron Lett., 42, 8619-8624.
208. (b) Krämer, C.S., Zimmermann, T.J., Sailer M., and Müller, T.J.J. (2002) Synthesis, 1163-1170.
209. (c) Wegner, H.A., Scott, L.T., and Meijere, A.D. (2003) J. Org. Chem., 68, 883-887.
210. (d) Yu, L., Muthukumaran, K., Sazanovich, I.V., Kirmaier, C., Hindin, E., Diers, J.R., Boyle, P.D., Bocian, D.F., Holten, D., and Lindsey, J.S. (2003) Inorg. Chem., 42, 6629-6647.
211. (e) Schmittel, M. and Kishore, R.S.K. (2004) Org. Lett., 6, 1923-1926.
212. (f) Tam, V.K., Liu, Q., and Tor, Y. (2006) Chem. Commun., 2684-2686.
213. (g) Montes, V.A., Pohl, R., Shinar, J., and Anzenbacher, P., Jr. (2006) Chem. Eur. J., 12, 4523-4535.
214. (h) Ronan, D., Jeannerat, D., Pinto, A., Sakai, N., and Matile, S. (2006) New J. Chem., 30, 168-176.
215. (i) Saito, S., Yamaguchi, H., Muto, H., and Makino, T. (2007) Tetrahedron Lett., 48, 7498-7501.
216. (j) Takeuchi, T., Akeda, K., Murakami, S., Shinmori, H., Inoue, S., Lee, W.S., and Hishiya, T. (2007) Org. Biomol. Chem., 5, 2368-2374.
217. (k) Schiek, M., Al-Shamery, K., and Lützen, A. (2007) Synthesis, 613-621.
218. (l) Sakai, N., Sisson, A.L., Bhosale, S., Fürstenberg, A., Banerji, N., Vauthey, E., and Matile, S. (2007) Org. Biomol. Chem., 5, 2560-2563.
219. (m) Mora, F., Tran, D.-H., Oudry, N., Hopfgartner, G., Jeannerat, D., Sakai, N., and Matile, S. (2008) Chem. Eur. J., 14, 1947-1953.
220. (a) Takahashi, K., Takagi, J. Ishiyama, T., and Miyaura, N. (2000) Chem. Lett., 2, 126-127.
221. (b) Takagi, J., Takahashi, K., Ishiyama, T., and Miyaura, N. (2002) J. Am. Chem. Soc., 124, 8001-8006.
222. (a) Shimizu, T., Satoh, T., Murakoshi, K., and Sodeoka, M. (2005) Org. Lett., 7, 5573-5576.
223. (b) Gopalarathnam, A. and Nelson, S.G. (2006) Org. Lett., 8, 7-10.
224. Takagi, J., Kamon, A., Ishiyama, T., and Miyaura, N. (2002) Synlett, 1880-1882.
225. (a) Eastwood, P.R. (2000) Tetrahedron Lett., 41, 3705-3708.
226. (b) Jin, B., Liu, Q., and Sulikowski, G.A. (2005) Tetrahedron, 61, 401-408.
227. (c) Ghosh, S., Kinney, W.A., Gauthier, D.A., Lawson, E.C., Hudlicky, T., and Maryanoff, B.E. (2006) Can. J. Chem., 84, 555-560.
228. (d) López, S., Montenegro, J., and Saá, C. (2007) J. Org. Chem., 72, 9572-9581.
229. (e) Kohno, K., Azuma, S., Choshi, T., Nobuhiro, J., and Hibino, S. (2009) Tetrahedron Lett., 50, 590-592.
230. (a) Murata, M., Oyama, T., Watanabe, S., and Masuda, Y. (2000) Synthesis, 778-780.
231. (b) Lessard, S., Peng, F., and Hall, D.G. (2009) J. Am. Chem. Soc., 131, 9612-9613.
232. Winkler, J.D., Londregan, A.T., Ragains, J.R., and Hamann, M.T. (2006) Org. Lett., 8, 3407-3409.
233. Högermeier, J. and Reissig, H.U. (2006) Synlett, 2759-2762.
234. (a) Ferrali, A., Guarna, A.Galbo, F.L., and Occhiato, E.G. (2004) Tetrahedron Lett., 45, 5271-5274.
235. (b) Occhiato, E.G., Galbo, F.L., and Guarna, A. (2005) J. Org. Chem., 70, 7324-7330.
236. Ishiyama, T., Ahiko, T.-a., and Miyaura, N. (1996) Tetrahedron Lett., 37, 6889-6892.
237. Dutheuil, G., Selander, N., Szabó, K.J., and Aggarwal, V.K. (2008) Synthesis, 2293-2297.
238. Ahiko, T.-a., Ishiyama, T., and Miyaura, N. (1997) Chem. Lett., 811-812.
239. (a) Ramachandran, P.V., Pratihar, D., Biswas, D., Srivastava, A., and Reddy, M.V.R. (2004) Org. Lett., 6, 481-484.
240. (b) Kabalka, G.W., Venkataiah, B., and Dong, G. (2004) J. Org. Chem., 69, 5807-5809.
241. Mitra, S., Gurrala, S.R., and Coleman, R.S. (2007) J. Org. Chem., 72, 8724-8736.
242. (a) Ito, H., Kawakami, C., and Sawamura, M. (2005) J. Am. Chem. Soc., 127, 16034-16035.
243. (b) Ito, H., Ito, S., Sasaki, Y., Matsuura, K., and Sawamura, M. (2007) J. Am. Chem. Soc., 129, 14856-14857.
244. (c) Ito, H., Sasaki, Y., and Sawamura, M. (2008) J. Am. Chem. Soc., 130, 15774-15775.
245. Ishiyama, T., Oohashi, Z., Ahiko, T.-a., and Miyaura, N. (2002) Chem. Lett., 780-781.
246. Giroux, A. (2003) Tetrahedron Lett., 44, 233-235.
247. (a) Waltz, K.M. and Hartwig, J.F. (1997) Science, 277, 211-213.
248. (b) Waltz, K.M., Muhoro, C.N., and Hartwig, J.F. (1999) Organometallics, 18, 3383-3393.
249. Chen, H.Y. and Hartwig, J.F. (1999) Angew Chem., Int. Ed., 38, 3391-3393.
250. (a) Kawamura, K. and Hartwig, J.F. (2001) J. Am. Chem. Soc., 123, 8422-8423.
251. (b) Lawrence, J.D., Takahashi, M., Bae, C., and Hartwig, J.F. (2004) J. Am. Chem. Soc., 126, 15334-15335.
252. (c) Hartwig, J.F., Cook, K.S., Hapke, M.D., Incarvito, C., Fan, Y., Webster, C.E., and Hall, M.B. (2005) J. Am. Chem. Soc., 127, 2538-2552.
253. (d) Boebel, T.A. and Hartwig, J.F. (2008) Organometallics, 27, 6013-6019.
254. Murphy, J.M., Lawrence, J.D., Kawamura, K., Incarvito, C., and Hartwig, J.F. (2006) J. Am. Chem. Soc., 128, 13684-13685.
255. Kondo, Y., Garcia-Guadrado, D., Hartwig, J.F., Boaen, N.K., Wagner, N.L., and Hillmyer, M.A. (2002) J. Am. Chem. Soc., 124, 1164-1165.
256. Olsson, V.J. and Szabó, K.J. (2007) Angew. Chem., Int. Ed., 46, 6891-6893.
257. Shimada, S., Batsanov, A.S., Howard, J.A.K., and Marder, T.B. (2001) Angew Chem., Int. Ed., 40, 2168-2171.
258. Ishiyama, T., Ishida, K., Takagi, J., and Miyaura, N. (2001) Chem. Lett., 1082-1083.
259. (a) Kikuchi, T., Takagi, J., Ishiyama, T., and Miyaura, N. (2008) Chem. Lett., 37, 664-665.
260. (b) Kikuchi, T., Takagi, J., Isou, H., Ishiyama, T., and Miyaura, N. (2008) Chem. Asian. J., 3, 2082-2090.
261. Chen, H., Schlecht, S., Semple, T.C., and Hartwig, J.F. (2000) Science, 287, 1995-1997.
262. Cho, J.-Y., Iverson, C.N., and Smith, M.R., III (2000) J. Am. Chem. Soc., 122, 12868-12869.
263. Tse, M.K., Cho, J.-Y., and Smith, M.R., III (2001) Org. Lett., 3, 2831-2833.
264. (a) Iverson, C.N. and Smith, M.R., III (1999) J. Am. Chem. Soc., 121, 7696-7697.
265. (b) Cho, J.-Y., Tse, M.K., Holmes, D., Maleczka, R.E., Jr., and Smith, M.R., III (2002) Science, 295, 305-307.
266. (c) Holmes, D., Chotana, G.A., Maleczka, R.E., Jr., and Smith, M.R., III (2006) Org. Lett., 8, 1407-1410
267. (d) Lokare, K.S., Staples, R.J., and Odom, A.L. (2008) Organometallics, 27, 5130-5138.
268. (a) Takagi, J., Sato, K., Hartwig, J.F., Ishiyama, T., and Miyaura, N. (2002) Tetrahedron Lett., 43, 5649-5651.
269. (b) Liversedge, I.A., Higgins, S.J., Giles, M., Heeney, M., and McCulloch, I. (2006) Tetrahedron Lett., 47, 5143-5146.
270. (c) Stockmann, V., Eriksen, K., and Fiksdahl, L.A. (2008) Tetrahedron, 64, 11180-11184.
271. (a) Ishiyama, T., Takagi, J., Hartwig, J.F., and Miyaura, N. (2002) Angew Chem., Int. Ed., 41, 3056-3058.
272. (b) Ishiyama, T., Takagi, J., Yonekawa, Y., Hartwig, J.F., and Miyaura, N. (2003) Adv. Synth. Catal., 345, 1103-1106.
273. (c) Shi, F., Smith, M.R., III, and Maleczka, R.E., Jr. (2006) Org. Lett., 8, 1411-1414.
274. (d) Tzschucke, C.C., Murphy, J.M., and Hartwig, J.F. (2007) Org. Lett., 9, 761-767.
275. (e) Harrison, P., Morris, L., Marder, T.B., and Steel, P.G. (2009) Org. Lett., 11, 3586-3589.
276. Ishiyama, T., Nobuta, Y., Hartwig, J.F., and Miyaura, N. (2003) Chem. Commun., 2924-2925.
277. Murata, M., Odajima, H., Watanabe, S., and Masuda, Y. (2006) Bull. Chem. Soc. Jpn., 79, 1980-1982.
278. Tagata, T. and Nishida, M. (2004) Adv. Synth. Catal., 346, 1655-1660.
279. Frey, G.D., Rentzsch, C.F., Preysing, D.V., Scherg, T., Muhlhofer, M., Herdtweck, E., and Herrmann, W.A. (2006) J. Organomet. Chem., 691, 5725-5738.
280. Tagata, T., Nishida, M., and Nishida, A. (2009) Tetrahedron Lett., 50, 6176-6179.
281. Finke, A.D. and Moore, J.S. (2008) Org. Lett., 10, 4851-4854.
282. Cordes, J., Wessel, C., Harms, K., and Koert, U. (2008) Synthesis, 2217-2220.
283. (a) Coventry, D.N., Batsanov, A.S., Goeta, A.E., Howard, J.A.K., Marder, T.B., and Perutz, R.N. (2005) Chem. Commun., 22, 2172-2174.
284. (b) Wanninger-Weib, B.C. and Wagenknecht, H.-A. (2008) Eur. J. Org. Chem., 64-71.
285. Chotana, G.A., Rak, M.A., and Smith, M.R., III (2005) J. Am. Chem. Soc., 127, 10539-10544.
286. Datta, A., Kollhofer, A., and Plenio, H. (2004) Chem. Commun., 21, 1508-1509.
287. Kurotobi, K., Miyauchi, M., Takakura, K., Murafuji, T., and Sugihara, Y. (2003) Eur. J. Org. Chem., 3663-3665.
288. Chotana, G.A., Kallepalli, V.A. Maleczka, R.E., Jr., and Smith, M.R., III (2008) Tetrahedron, 64, 6103-6114.
289. Ishida, N., Narumi, M., and Murakami, M. (2008) Org. Lett., 10, 1279-1281.
290. Mkhalid, I.A.I., Coventry, D.N., Albesa-Jove, D., Batsanov, A.S., Howard, J.A.K., Perutz, R.N., and Marder, T.B. (2006) Angew. Chem., Int. Ed., 45, 489-491.
291. (a) Paul, S., Chotana, G.A., Holmes, D., Reichle, R.C., Maleczka, R.E., Jr., and Smith, M.R., III (2006) J. Am. Chem. Soc., 128, 15552-15553.
292. (b) Lo, W.F., Kaiser, H.M., Spannenberg, A., Beller, M., and Tse, M.K. (2007) Tetrahedron Lett., 48, 371-375.
293. (a) Hata, H., Shinokubo, H., and Osuka, A. (2005) J. Am. Chem. Soc., 127, 8264-8265.
294. (b) Hata, H., Yamaguchi, S., Mori, G., Nakazono, S., Katoh, T., Takatsu, K., Hiroto, S., Shinokubo, H., and Osuka, A. (2007) Chem. Asian J., 2, 849-859; (c) Mori, G., Shinokubo, H., and Osuka, A. (2008) Tetrahedron Lett., 49, 2170-2172.
295. (c) Mori, G., Shinokubo, H., and Osuka, A. (2008) Tetrahedron Lett., 49, 2170-2172.
296. Ohmura, T., Kijima, A., and Suginome, M. (2009) J. Am. Chem. Soc., 131, 6070-6071.
297. Boebel, T.A. and Hartwig, J.F. (2008) J. Am. Chem. Soc., 130, 7534-7535.
298. Ishiyama, T., Isou, H., Kikuchi, T., and Miyaura, N. (2010) Chem. Commun., 46, 159-161.
299. (a) Caron, S. and Hawkins, J.M. (1998) J. Org. Chem., 63, 2054-2055.
300. (b) Kristensen, J., Lysén, M., Vedsø, P., and Begtrup, M. (2001) Org. Lett., 3, 1435-1437.