Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 941-951
http://dx.doi.org/10.1351/pac200880050941
Carbon-carbon bond-forming reactions using alkyl fluorides
References
- 1. (a). S. Murai. In Activation of Unreactive Bonds and Organic Synthesis, pp. 243-269, Springer, New York (1999);
- 1. (b). T. Hiyama. In Organofluorine Compounds Chemistry and Applications, Springer, New York (2000).
- 2. (a). Y. Kiso, K. Tamao, M. Kumada. J. Organomet. Chem. 50, C12 (1973); (http://dx.doi.org/10.1016/S0022-328X(00)95063-0)
- 2. (b). M. Aizenberg, D. Milstein. Science 265, 359 (1994); (http://dx.doi.org/10.1126/science.265.5170.359)
- 2. (c). G. B. Deacon, C. M. Forsyth, J. Sun. Tetrahedron Lett. 35, 1095 (1994); (http://dx.doi.org/10.1016/S0040-4039(00)79974-6)
- 2. (d). M. Aizenberg, D. Milstein. J. Am. Chem. Soc. 117, 8674 (1995); (http://dx.doi.org/10.1021/ja00138a027)
- 2. (e). Y. Ishii, N. Chatani, S. Yorimitsu, S. Murai. Chem. Lett. 157 (1998); (http://dx.doi.org/10.1246/cl.1998.157)
- 2. (f). J. Y. Robert Jr., V. G. Vladimir. Organometallics 18, 294 (1999); (http://dx.doi.org/10.1021/om980887w)
- 2. (g). H. Yang, H. Gao, J. R. Angelici. Organometallics 18, 2285 (1999); (http://dx.doi.org/10.1021/om990151e)
- 2. (h). B. L. Edelbach, B. M. Kraft, W. D. Jones. J. Am. Chem. Soc. 121, 10327 (1999); (http://dx.doi.org/10.1021/ja991805d)
- 2. (i). T. G. Richmond. Angew. Chem., Int. Ed. 39, 3241 (2000); (http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3241::AID-ANIE3241>3.0.CO;2-X)
- 2. (j). V. P. W. Bohm, C. W. K. Gstottmayr, T. Weskamp, W. A. Herrmann. Angew. Chem., Int. Ed. 40, 3387 (2001). (http://dx.doi.org/10.1002/1521-3773(20010917)40:18<3387::AID-ANIE3387>3.0.CO;2-6)
- 3. (a). R. G. Harrison, T. G. Richmond. J. Am. Chem. Soc. 115, 5303 (1993); (http://dx.doi.org/10.1021/ja00065a055)
- 3. (b). M. Weydert, R. A. Andersen, R. G. Bergmen. J. Am. Chem. Soc. 115, 8837 (1993); (http://dx.doi.org/10.1021/ja00072a046)
- 3. (c). J. L. Kiplinger, T. G. Richmond. Chem. Commun. 1115 (1996); (http://dx.doi.org/10.1039/cc9960001115)
- 3. (d). B. L. Edelbach, W. D. Jones. J. Am. Chem. Soc. 119, 7734 (1997). (http://dx.doi.org/10.1021/ja970723r)
- 4. (a). J. L. Kiplinger, T. G. Richmond. J. Am. Chem. Soc. 118, 1805 (1996); (http://dx.doi.org/10.1021/ja952563u)
- 4. (b). J. Burdeniuc, R. H. Crabtree. J. Am. Chem. Soc. 118, 2525 (1996); (http://dx.doi.org/10.1021/ja9539599)
- 4. (c). J. Burdeniuc, R. H. Crabtree. Organometallics 17, 1582 (1998); (http://dx.doi.org/10.1021/om970871q)
- 4. (d). B. M. Kraft, R. J. Lachicotte, W. D. Jones. J. Am. Chem. Soc. 122, 8559 (2000). (http://dx.doi.org/10.1021/ja001006r)
- 5. (a). T. Hatakeyama, S. Ito, M. Nakamura, E. Nakamura. J. Am. Chem. Soc. 127, 14192 (2005); (http://dx.doi.org/10.1021/ja055306q)
- 5. (b). K. Fuchibe, T. Akiyama. J. Am. Chem. Soc. 128, 1434 (2006); (http://dx.doi.org/10.1021/ja0565323)
- 5. (c). K. Fuchibe, K. Mitomi, T. Akiyama. Chem. Lett. 36, 24 (2007). (http://dx.doi.org/10.1246/cl.2007.24)
- 6. K. Fuchibe, Y. Ohshima, K. Mitomi, T. Akiyama. Org. Lett. 9, 1497 (2007). (http://dx.doi.org/10.1021/ol070249m)
- 7. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe. J. Am. Chem. Soc. 124, 4222 (2002). (http://dx.doi.org/10.1021/ja025828v)
- 8. (a). International Symposium on 30 years of the Cross-coupling Reaction, J. Organomet. Chem. 653, 1 (2002);
- 8. (b). F. Diederich, P. J. Stang (Eds.). Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, New York (1998).
- 9. J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe. J. Am. Chem. Soc. 125, 5646 (2003). (http://dx.doi.org/10.1021/ja034201p)
- 10. S. Tobisch. Adv. Organomet. Chem. 49, 167 (2003). (http://dx.doi.org/10.1016/S0065-3055(03)49005-9)
- 11. (a). P. A. Wender, M. J. Tebbe. Synthesis 1089 (1991); (http://dx.doi.org/10.1055/s-1991-28397)
- 11. (b). M. Takimoto, M. Mori. J. Am. Chem. Soc. 124, 10008 (2002). (http://dx.doi.org/10.1021/ja026620c)
- 12. J. Terao, H. Todo, H. Watanabe, A. Ikumi, N. Kambe. Angew. Chem., Int. Ed. 43, 6180 (2004). (http://dx.doi.org/10.1002/anie.200460246)
- 13. J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe. Angew. Chem., Int. Ed. 46, 2086 (2007). (http://dx.doi.org/10.1002/anie.200603451)
- 14. J. Terao, H. Watabe, N. Kambe. J. Am. Chem. Soc. 127, 3656 (2005). (http://dx.doi.org/10.1021/ja042565r)
- 15. (a). G. M. Whitesides, C. P. Casey. J. K. Krieger. J. Am. Chem. Soc. 93, 1379 (1971); (http://dx.doi.org/10.1021/ja00735a011)
- 15. (b). M. F. Semmelhack, P. Helquist, L. D Jones, L. Keller, L. Mendelson, L. S. Ryono, J. G. Smith, R. D. Stauffer. J. Am. Chem. Soc. 103, 6460 (1981). (http://dx.doi.org/10.1021/ja00411a034)
- 16. W. Kaschube, K. R. Porschke. K. Angermund, C. Kruger. G. Wilke. Chem. Ber. 121, 1921 (1988).
- 17. J. Terao, K. Torii, K. Saito, N. Kambe, A. Baba, N. Sonoda. Angew. Chem., Int. Ed. 37, 2653 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2653::AID-ANIE2653>3.0.CO;2-3)
- 18. J. Terao, T. Watanabe, K. Saito, N. Kambe, N. Sonoda. Tetrahedron Lett. 39, 9201 (1998). (http://dx.doi.org/10.1016/S0040-4039(98)02097-8)
- 19. (a). E. Negishi, F. E. Cederbaum, T. Takahashi. Tetrahedron Lett. 27, 2829 (1986); (http://dx.doi.org/10.1016/S0040-4039(00)84653-5)
- 19. (b). F. Soleil, R. Choukroun. J. Am. Chem. Soc. 119, 2938 (1997); (http://dx.doi.org/10.1021/ja962355h)
- 19. (c). V. K. Dioumaev, J. F. Harrod. Organometallics 16, 1452 (1997). (http://dx.doi.org/10.1021/om960543a)
- 20. T. Takahashi, N. Suzuki, M. Kageyama, Y. Nitto, M. Saburi, E. Negish. Chem. Lett. 1579 (1991). (http://dx.doi.org/10.1246/cl.1991.1579)
- 21. E. Negish, T. Nguyen, J. P. Maye, D. Choueiri, N. Suzuki, T. Takahashi. Chem. Lett. 2367 (1992). (http://dx.doi.org/10.1246/cl.1992.2367)
- 22. J. Terao, S. A. Begum, A. Oda, N. Kambe. Synlett 1783 (2005).
- 23. (a). P. Tarrant, R. N. Bull. J. Fluorine Chem. 40, 201 (1988); (http://dx.doi.org/10.1016/S0022-1139(00)83066-3)
- 23. (b). B. Kosmrlj, B. Kralj, B. Sket. Tetrahedron Lett. 36, 7921 (1995); (http://dx.doi.org/10.1016/0040-4039(95)01642-U)
- 23. (c). G. H. Posner, G. M. Gurria, K. A. Babiak. J. Org. Chem. 42, 3173 (1997); (http://dx.doi.org/10.1021/jo00439a014)
- 23. (d). T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka. Tetrahedron Lett. 38, 5679 (1997); (http://dx.doi.org/10.1016/S0040-4039(97)01237-9)
- 23. (e). K. Toshima. Carbohydr. Res. 327, 15 (2000); (http://dx.doi.org/10.1016/S0008-6215(99)00325-0)
- 23. (f). V. A. Petrov. J. Fluorine Chem. 117, 23 (2002); (http://dx.doi.org/10.1016/S0022-1139(02)00165-3)
- 23. (g). M. Yoshimatsu, M. Kawamoto, K. Gotoh. Eur. J. Org. Chem. 14, 2884 (2005). (http://dx.doi.org/10.1002/ejoc.200500179)
- 24. (a). J. S. Filippo Jr., A. F. Sowinski, L. J. Romano. J. Org. Chem. 40, 3295 (1975); (http://dx.doi.org/10.1021/jo00910a034)
- 24. (b). G. A. Olah, S. C. Narang, L. D. Field. J. Org. Chem. 46, 3727 (1981); (http://dx.doi.org/10.1021/jo00331a030)
- 24. (c). M. Namavari, N. Satyamurthy, J. R. Barrio. J. Fluorine Chem. 72, 89 (1995). (http://dx.doi.org/10.1016/0022-1139(94)03193-4)
- 25. G. H. Posner, S. R. Haines. Tetrahedron Lett. 26, 1823 (1985). (http://dx.doi.org/10.1016/S0040-4039(00)94747-6)
- 26. K. Hirano, K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima. Tetrahedron Lett. 45, 2555 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.01.145)
- 27. J. Terao, S. A. Begum, Y. Shinohara, M. Tomita, Y. Naitoh, N. Kambe. Chem. Commun. 855 (2007). (http://dx.doi.org/10.1039/b613641a)