Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 807-817
http://dx.doi.org/10.1351/pac200880050807
1,4-Additions of arylboron, -silicon, and -bismuth compounds to α,β-unsaturated carbonyl compounds catalyzed by dicationic palladium(II) complexes
References
- 1. (a). E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.). Comprehensive Asymmetric Catalysis, Chaps. 29.3, 31.1, and 31.2, Springer, Berlin (1999);
- 1. (b). N. Krause, A. Hoffmann-Roder. Synthesis 171 (2001); (http://dx.doi.org/10.1055/s-2001-10803)
- 1. (c). K. Fagnou, M. Lautens. Chem. Rev. 103, 169 (2003); (http://dx.doi.org/10.1021/cr020007u)
- 1. (d). T. Hayashi, K. Yamasaki. Chem. Rev. 103, 2829 (2003). (http://dx.doi.org/10.1021/cr020022z)
- 2. (a). A. de Meijere, F. Diederich (Eds.). Metal-Catalyzed Cross-Coupling Reactions: Second, Completely Revised and Enlarged Edition, Wiley-VCH, Weinheim (2004);
- 2. (b). N. Miyaura (Ed.). Cross-Coupling Reactions: A Practical Guide, Springer, Berlin (2002);
- 2. (c). A. Suzuki, H. C. Brown. Organic Syntheses Via Boranes, Vol. 3, Suzuki Coupling, Aldrich Chemical Co., Milwaukee (2003);
- 2. (d). A. Suzuki. J. Organomet. Chem. 576, 147 (1998); (http://dx.doi.org/10.1016/S0022-328X(98)01055-9)
- 2. (e). N. Miyaura, A. Suzuki. Chem. Rev. 95, 2457 (1995); (http://dx.doi.org/10.1021/cr00039a007)
- 2. (f). T. Hiyama, Y. Hatanaka. Pure Appl. Chem. 66, 1471 (1994); (http://dx.doi.org/10.1351/pac199466071471)
- 2. (g). Y. Hatanaka, T. Hiyama. Synlett 845 (1991). (http://dx.doi.org/10.1055/s-1991-20899)
- 3. (a). T. Nishikata, Y. Yamamoto, N. Miyaura. Angew. Chem., Int. Ed. 42, 2768 (2003); (http://dx.doi.org/10.1002/anie.200350888)
- 3. (b). T. Nishikata, Y. Yamamoto, N. Miyaura. Chem. Lett. 32, 752 (2003); (http://dx.doi.org/10.1246/cl.2003.752)
- 3. (c). T. Nishikata, Y. Yamamoto, N. Miyaura. Organometallics 23, 4314 (2004); (http://dx.doi.org/10.1021/om0498044)
- 3. (d). T. Nishikata, Y. Yamamoto, N. Miyaura. Chem. Commun. 1822 (2004); (http://dx.doi.org/10.1039/b407272c)
- 3. (e). T. Nishikata, Y. Yamamoto, N. Miyaura. Chem. Lett. 34, 720 (2005); (http://dx.doi.org/10.1246/cl.2005.720)
- 3. (f). T. Nishikata, Y. Yamamoto, I. D. Gridnev, N. Miyaura. Organometallics 24, 5025 (2005); (http://dx.doi.org/10.1021/om050678t)
- 3. (g). T. Nishikata, Y. Yamamoto, N. Miyaura. Adv. Synth. Catal. 349, 1759 (2007); (http://dx.doi.org/10.1002/adsc.200600622)
- 3. (h). T. Nishikata, Y. Yamamoto, N. Miyaura. Tetrahedron Lett. 48, 4007 (2007). (http://dx.doi.org/10.1016/j.tetlet.2007.04.038)
- 4. (a). M. Sakai, H. Hayashi, N. Miyaura. Organometallics 16, 4229 (1997); (http://dx.doi.org/10.1021/om9705113)
- 4. (b). Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura. J. Am. Chem. Soc. 120, 5579 (1998); (http://dx.doi.org/10.1021/ja980666h)
- 4. (c). S. Sakuma, M. Sakai, R. Itooka, N. Miyaura. J. Org. Chem. 65, 5951 (2000); (http://dx.doi.org/10.1021/jo0002184)
- 4. (d). R. Itooka, Y. Iguchi, N. Miyaura. Chem. Lett. 722 (2001); (http://dx.doi.org/10.1246/cl.2001.722)
- 4. (e). S. Sakuma, N. Miyaura. J. Org. Chem. 66, 8944 (2001); (http://dx.doi.org/10.1021/jo010747n)
- 4. (f). Y. Yamamoto, M. Fujita, N. Miyaura. Synlett 767 (2002); (http://dx.doi.org/10.1055/s-2002-25371)
- 4. (g). R. Itooka, Y. Iguchi, N. Miyaura. J. Org. Chem. 68, 6000 (2003); (http://dx.doi.org/10.1021/jo0207067)
- 4. (h). Y. Iguch, R. Itooka, N. Miyaura. Synlett 1040 (2003);
- 4. (i). Y. Yamamoto, K. Kurihara, N. Sugishita, K. Oshita, D. Piao, N. Miyaura. Chem. Lett. 1224 (2005); (http://dx.doi.org/10.1246/cl.2005.1224)
- 4. (j). T. Itoh, T. Mase, T. Nishikata, T. Iyama, H. Tachikawa, Y. Kobayashi, Y. Yamamoto, N. Miyaura. Tetrahedron 62, 9610 (2006); (http://dx.doi.org/10.1016/j.tet.2006.07.075)
- 4. (k). K. Kurihara, N. Sugishita, K. Oshita, D. Piao, Y. Yamamoto, N. Miyaura. J. Organomett. Chem. 692, 428 (2007). (http://dx.doi.org/10.1016/j.jorganchem.2006.04.042)
- 5. (a). R. A. Batey, A. N. Thadani, D. V. Smil. Org. Lett. 1, 1683 (1999); (http://dx.doi.org/10.1021/ol9910767)
- 5. (b). T. Hayashi, T. Senda, Y. Takaya, M. Ogasawara. J. Am. Chem. Soc. 121, 11591 (1999); (http://dx.doi.org/10.1021/ja993184u)
- 5. (c). T. Hayashi, T. Senda, M. Ogasawara. J. Am. Chem. Soc. 122, 10716 (2000); (http://dx.doi.org/10.1021/ja002805c)
- 5. (d). M. T. Reetz, D. Moulin, A. Gosberg. Org. Lett. 3, 4083 (2001); (http://dx.doi.org/10.1021/ol010219y)
- 5. (e). J. O. Ramnaulth, S. S. Poulin, S. Bratovanov, S. Rakhit, P. Maddaford. Org. Lett. 3, 2571 (2001); (http://dx.doi.org/10.1021/ol016245d)
- 5. (f). R. Amengual, V. Michelet, J.-P. Genet. Tetrahedron Lett. 43, 5905 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)01274-1)
- 5. (g). M. Pucheault, S. Darses, J.-P. Genet. Tetrahedron Lett. 43, 6155 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)01288-1)
- 5. (h). T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara. J. Am. Chem. Soc. 124, 5052 (2002); (http://dx.doi.org/10.1021/ja012711i)
- 5. (i). M. Kuriyama, K. Nagai, K. Yamada, Y. Miwa, T. Taga, K. Tomioka. J. Am. Chem. Soc. 124, 8932 (2002); (http://dx.doi.org/10.1021/ja0261933)
- 5. (j). Y. Ma, C. Song, C. Ma, Z. Sun, Q. Chai, M. B. Andrus. Angew. Chem., Int. Ed. 42, 5871 (2003); (http://dx.doi.org/10.1002/anie.200352679)
- 5. (k). D. F. Cauble, J. D. Gipson, M. J. Krische. J. Am. Chem. Soc. 125, 1110 (2003); (http://dx.doi.org/10.1021/ja0211095)
- 5. (l). C. J. Chapman, C. G. Frost. Adv. Synth. Catal. 345, 353 (2003); (http://dx.doi.org/10.1002/adsc.200390039)
- 5. (m). Y. Ma, C. Song, C. Ma, Z. Sun, Q. Chai, M. B. Andrus. Angew. Chem., Int. Ed. 42, 5871 (2003); (http://dx.doi.org/10.1002/anie.200352679)
- 5. (n). J.-G. Boiteau, A. J. Minnaard, B. L. Feringa. J. Org. Chem. 68, 9481 (2003); (http://dx.doi.org/10.1021/jo035155e)
- 5. (o). P. Mauleon, J. C. Carretero, Org. Lett. 6, 3195 (2004); (http://dx.doi.org/10.1021/ol048690p)
- 5. (p). C. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira. Org. Lett. 6, 3873 (2004); (http://dx.doi.org/10.1021/ol048240x)
- 5. (q). M. Pucheault, V. Michaut, S. Darses, J.-P. Genet. Tetrahedron Lett. 45, 4729 (2004); (http://dx.doi.org/10.1016/j.tetlet.2004.04.075)
- 5. (r). A. Cuursma, J.-G. Boiteau, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa. J. Org. Chem. 69, 8045 (2004); (http://dx.doi.org/10.1021/jo0487810)
- 5. (s). L. Navarre, M. Pucheault, S. Darses, J.-P. Genet. Tetrahedron Lett. 46, 4247 (2005); (http://dx.doi.org/10.1016/j.tetlet.2005.04.038)
- 5. (t). G. Chen, N. Tokunaga, T. Hayashi. Org. Lett. 7, 2285 (2005); (http://dx.doi.org/10.1021/ol0507367)
- 5. (u). K. Vandyck, B. Matthys, M. Willen, K. Robeyns, L. V. Meervelt, J. V. der Eycken. Org. Lett. 8, 363 (2006); (http://dx.doi.org/10.1021/ol0522788)
- 5. (v). T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida. J. Am. Chem. Soc. 125, 11506 (2003); (http://dx.doi.org/10.1021/ja035121o)
- 5. (w). R. Shintani, N. Tokunaga, H. Doi, T. Hayashi. J. Am. Chem. Soc. 126, 6240 (2004). (http://dx.doi.org/10.1021/ja048825m)
- 6. (a). A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada. J. Am. Chem. Soc. 123, 10774 (2001); (http://dx.doi.org/10.1021/ja015928l)
- 6. (b). T.-S. Huang, C.-J. Li. Chem. Commun. 2348 (2001); (http://dx.doi.org/10.1039/b106768k)
- 6. (c). S. Oi, Y. Honma, Y. Inoue. Org. Lett. 4, 667 (2002); (http://dx.doi.org/10.1021/ol025518h)
- 6. (d). M. Murata, R. Shimazaki, M. Ishikura, S. Watanabe, Y. Masuda. Synthesis 717 (2002); (http://dx.doi.org/10.1055/s-2002-25764)
- 6. (e). T. Koike, X. Du, A. Mori, K. Osakada. Synlett 301 (2002); (http://dx.doi.org/10.1055/s-2002-19787)
- 6. (f). S. Oi, A. Taira, Y. Honma, Y. Inoue. Org. Lett. 5, 97 (2003). (http://dx.doi.org/10.1021/ol0272904)
- 7. (a). S. Oi, M. Moro, S. Ono, Y. Inoue. Chem. Lett. 83 (1998); (http://dx.doi.org/10.1246/cl.1998.83)
- 7. (b). T.-S. Huang, C.-J. Li. Org. Lett. 3, 2037 (2001); (http://dx.doi.org/10.1021/ol010079s)
- 7. (c). T. Huang, Y. Meng, S. Venkatraman, D. Wang, C.-J. Li. J. Am. Chem. Soc. 123, 7451 (2001); (http://dx.doi.org/10.1021/ja015561k)
- 7. (d). S. Oi, M. Moro, H. Ito, Y. Honma, S. Miyano, Y. Inoue. Tetrahedron 58, 91 (2002); (http://dx.doi.org/10.1016/S0040-4020(01)01128-0)
- 7. (e). T.-S. Huang, C.-J. Li. Org. Lett. 3, 2037 (2001). (http://dx.doi.org/10.1021/ol010079s)
- 8. (a). T. Hayashi, N. Tokunaga, K. Yoshida, J. W. Han. J. Am. Chem. Soc. 124, 12102 (2002); (http://dx.doi.org/10.1021/ja027663w)
- 8. (b). K. Yoshida, T. Hayashi. J. Am. Chem. Soc. 125, 2872 (2003); (http://dx.doi.org/10.1021/ja0295568)
- 8. (c). T. Hayashi. Bull. Chem. Soc. Jpn. 77, 13 (2004). (http://dx.doi.org/10.1246/bcsj.77.13)
- 9. (a). R. Shintani, N. Tokunaga, H. Doi, T. Hayashi. J. Am. Chem. Soc. 126, 6240 (2004); (http://dx.doi.org/10.1021/ja048825m)
- 9. (b). A. Kina, K. Ueyama, T. Hayashi. Org. Lett. 7, 5889 (2005); (http://dx.doi.org/10.1021/ol0524914)
- 9. (c). R. Shintani, T. Yamagami, T. Kimura, T. Hayashi. Org. Lett. 7, 5317 (2005). (http://dx.doi.org/10.1021/ol052257d)
- 10. (a). A. Kakuuchi, T. Taguchi, Y. Hanzawa. Tetrahedron 60, 1293 (2004); (http://dx.doi.org/10.1016/j.tet.2003.08.073)
- 10. (b). S. Oi, T. Sato, Y. Inoue. Tetrahedron Lett. 45, 5051 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.04.171)
- 11. In: T. Miura, M. Murakami. Chem. Commun. 5676 (2005). (http://dx.doi.org/10.1039/b511779h)
- 12. (a). K. Oguma, M. Miura, T. Satoh, M. Nomura. J. Am. Chem. Soc. 122, 10464 (2000); (http://dx.doi.org/10.1021/ja002601w)
- 12. (b). M. Lautens, A. Roy, K. Fukuoka, K. Fagnou, B. Martin-Matute. J. Am. Chem. Soc. 123, 5358 (2001); (http://dx.doi.org/10.1021/ja010402m)
- 12. (c). T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara. J. Am. Chem. Soc. 123, 9918 (2001); (http://dx.doi.org/10.1021/ja0165234)
- 12. (d). M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki. Org. Lett. 4, 1311 (2002); (http://dx.doi.org/10.1021/ol0256062)
- 12. (e). M. Murakami, H. Igawa. Chem. Commun. 390 (2002); (http://dx.doi.org/10.1039/b108808d)
- 12. (f). M. Lautens, M. Yoshida. Org. Lett. 4, 123 (2002); (http://dx.doi.org/10.1021/ol010261t)
- 12. (g). M. Lautens, T. Marquardt. J. Org. Chem. 69, 4607 (2004); (http://dx.doi.org/10.1021/jo049722p)
- 12. (h). M. Lautens, J. Mancuso. J. Org. Chem. 69, 3478 (2004). (http://dx.doi.org/10.1021/jo049874k)
- 13. (a). M. Sakai, M. Ueda, N. Miyaura. Angew Chem., Int. Ed. 37, 3279 (1998); (http://dx.doi.org/10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M)
- 13. (b). M. Ueda, N. Miyaura. J. Org. Chem. 65, 4450 (2000); (http://dx.doi.org/10.1021/jo000187c)
- 13. (c). A. Takezawa, K. Yamaguchi, T. Ohmura, Y. Yamamoto, N. Miyaura. Synlett 1733 (2002).
- 14. (a). S. Oi, M. Moro, Y. Inoue. J. Chem. Soc., Chem. Commun. 1621 (1997);
- 14. (b). S. Oi, M. Moro, H. Fukuhara, T. Kawanishi, Y. Inoue. Tetrahedron Lett. 40, 9259 (1999); (http://dx.doi.org/10.1016/S0040-4039(99)01857-2)
- 14. (c). C.-J. Li, Y. Meng. J. Am. Chem. Soc. 122, 9538 (2000); (http://dx.doi.org/10.1021/ja001699b)
- 14. (d). A. Furstner, H. Krause. Adv. Synth. Catal. 343 (2001); (http://dx.doi.org/10.1002/1615-4169(20010430)343:4<343::AID-ADSC343>3.0.CO;2-Z)
- 14. (e). S. Oi, M. Moro, Y. Inoue. Organometallics 20, 1036 (2001); (http://dx.doi.org/10.1021/om0009684)
- 14. (f). C. Moreau, C. Hague, A. S. Weller, C. G. Frost. Tetrahedron Lett. 42, 6957 (2001); (http://dx.doi.org/10.1016/S0040-4039(01)01421-6)
- 14. (g). T. Fujii, T. Koike, A. Mori, K. Osakada. Synlett 298 (2002); (http://dx.doi.org/10.1055/s-2002-19786)
- 14. (h). Z. Wang, G. Zou, J. Tang. Chem. Commun. 1192 (2004); (http://dx.doi.org/10.1039/b401511h)
- 14. (i). T. Matsuda, M. Makino, M. Murakami. Org. Lett. 6, 1257 (2004); (http://dx.doi.org/10.1021/ol049833a)
- 14. (j). N. Imlinger, M. Mayr, D. Wang, K. Wurst, M. R. Buchmeiser. Adv. Synth. Catal. 346, 1836 (2004); (http://dx.doi.org/10.1002/adsc.200404176)
- 14. (k). M. Pucheault, S. Darses, J.-P. Genet. J. Am. Chem. Soc. 126, 15356 (2004); (http://dx.doi.org/10.1021/ja044749b)
- 14. (l). T. Focken, J. Rudolph, C. Bolm. Synthesis 429 (2005).
- 15. (a). M. Ueda, N. Miyaura. J. Organomet. Chem. 595, 31 (2000); (http://dx.doi.org/10.1016/S0022-328X(99)00562-8)
- 15. (b). M. Ueda, A. Saito, N. Miyaura. Synlett 1637 (2000).
- 16. (a). S. Oi, M. Moro, H. Fukuhara, T. Kawanishi, Y. Inoue. Tetrahedron Lett. 40, 9259 (1999); (http://dx.doi.org/10.1016/S0040-4039(99)01857-2)
- 16. (b). T. Hayashi, M. Ishigedani. J. Am. Chem. Soc. 122, 976 (2000); (http://dx.doi.org/10.1021/ja9927220)
- 16. (c). A. Kakuchi, T. Taguchi, Y. Hanzawa. Tetrahedron Lett. 44, 923 (2003); (http://dx.doi.org/10.1016/S0040-4039(02)02767-3)
- 16. (d). M. Kuriyama, T. Soeta, X. Hao, Q. Chen, K. Tomioka. J. Am. Chem. Soc. 126, 8128 (2004); (http://dx.doi.org/10.1021/ja0475398)
- 16. (e). T. Miura, H. Nakagawa, M. Murakamai. Chem. Commun. 2855 (2005). (http://dx.doi.org/10.1039/b503686k)
- 17. (a). X. Lu, S. J. Lin. J. Org. Chem. 70, 9651 (2005); (http://dx.doi.org/10.1021/jo051561h)
- 17. (b). F. Gini, B. Hessen, A. Minnaard. Org. Lett. 7, 5309 (2005); (http://dx.doi.org/10.1021/ol052222d)
- 17. (c). T. Yamamoto, T. Ohta, Y. Ito. Org. Lett. 7, 4153 (2005); (http://dx.doi.org/10.1021/ol051501y)
- 17. (d). T. Yamamoto, M. Iizuka, T. Ohta, Y. Ito. Chem. Lett. 35, 198 (2006); (http://dx.doi.org/10.1246/cl.2006.198)
- 17. (e). Y. Suzuma, T. Yamamoto, T. Ohta, Y. Ito. Chem. Lett. 36, 470 (2007). (http://dx.doi.org/10.1246/cl.2007.470)
- 18. (a). Mechanisms of transmetallation were discussed in ref. [3c] and see also, chapters 1, 2, and 4 in ref. [2a];
- 18. (b). B. Crociani, F. D. Bianca, P. Uguagliati, L. Canovese, A. Berton. J. Chem. Soc., Dalton Trans. 71 (1991). (http://dx.doi.org/10.1039/dt9910000071)
- 19. A. Yamamoto. J. Organomet. Chem. 500, 337 (1995). (http://dx.doi.org/10.1016/0022-328X(95)00521-Q)
- 20. (a). J. E. Lynch, W.-B. Choi, H. R. O. Churchill, R. P. Volante, R. A. Reamer, R. G. Ball. J. Org. Chem. 62, 9223 (1997); (http://dx.doi.org/10.1021/jo971476c)
- 20. (b). R. P. Alexander, G. J. Warrellow, M. A. W. Eaton, E. C. Boyd, J. C. Head, J. R. Porter, J. A. Brown, J. T. Reuberson, B. Hutchinson, P. Turner, B. Boyce, D. Barnes, B. Mason, A. Cannell, R. J. Taylor, A. Zomaya, A. Millican, J. Leonard, R. Morphy, M. Wales, M. Perry, R. A. Allen, N. Gozzard, B. Hughes, G. Higgs. Bioorg. Med. Chem. Lett. 12, 1451 (2002); (http://dx.doi.org/10.1016/S0960-894X(02)00202-0)
- 20. (c). V. K. Aggarwal, I. Bae, H.-Y. Lee, J. Richardson, D. T. Williams. Angew. Chem., Int. Ed. 42, 3274 (2003). (http://dx.doi.org/10.1002/anie.200350968)
- 21. S. Cacchi, D. Miiti, G. Palmieri. J. Org. Chem. 47, 2995 (1982). (http://dx.doi.org/10.1021/jo00136a036)
- 22. G. Chen, N. Tokunaga, T. Hayashi. Org. Lett. 7, 2285 (2005). (http://dx.doi.org/10.1021/ol0507367)
- 23. T. Nishikata, Y. Yamamoto, N. Miyaura. Chem. Lett. 36, 1442 (2007). (http://dx.doi.org/10.1246/cl.2007.1442)