Pure and Applied Chemistry

Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1443-1451

http://dx.doi.org/10.1351/PAC-CON-09-10-15

Published online 2010-05-05

Chelation-assisted carbonylation reactions catalyzed by Rh and Ru complexes

References

• 1. Reviews, see.
• 1a. M. T. Reetz. Angew. Chem., Int. Ed. 23, 556 (1984).
• 1b. A. H. Hoveyda, D. A. Evans, G. C. Fu. Chem. Rev. 93, 1307 (1993). (http://dx.doi.org/10.1021/cr00020a002)
• 2. H. B. Henbest, R. A. L. Wilson. J. Chem. Soc. 1958 (1959).
• 3. W. G. Dauben, G. H. Berezin. J. Am. Chem. Soc. 85, 468 (1963). (http://dx.doi.org/10.1021/ja00887a023)
• 4. L. N. Lewis, J. F. Smith. J. Am. Chem. Soc. 108, 2728 (1986). (http://dx.doi.org/10.1021/ja00270a036)
• 5. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani. Nature 366, 529 (1993). (http://dx.doi.org/10.1038/366529a0)
• 6. For recent reviews on chelation-assisted transformation, see.
• 6a. F. Kakiuchi, N. Chatani. Adv. Synth. Catal. 345, 1077 (2003). (http://dx.doi.org/10.1002/adsc.200303094)
• 6b. A. R. Dick, M. S. Sanford. Tetrahedron 62, 2439 (2006). (http://dx.doi.org/10.1016/j.tet.2005.11.027)
• 6c. K. Godula, D. Sames. Science 312, 67 (2006). (http://dx.doi.org/10.1126/science.1114731)
• 6d. D. Alberico, M. E. Scott, M. Lautens. Chem. Rev. 107, 174 (2007). (http://dx.doi.org/10.1021/cr0509760)
• 6e. L.-C. Campeau, D. R. Stuart, K. Fagnou. Aldrichim. Acta 40, 35 (2007).
• 6f. N. Chatani (Ed.). Directed Metallation: Topics in Organometallic Chemistry, Vol. 24, Springer, Berlin (2007).
• 6g. F. Kakiuchi, T. Kochi. Synthesis 3013 (2008). (http://dx.doi.org/10.1055/s-2008-1067256)
• 6h. W. Lyons, M. S. Sanford. Chem. Rev. 110, 1147 (2010). (http://dx.doi.org/10.1021/cr900184e)
• 7. Y. Ishii, N. Chatani, S. Yorimitsu, S. Murai. Chem. Lett. 157 (1998). (http://dx.doi.org/10.1246/cl.1998.157)
• 8. N. Chatani, Y. Ie, F. Kakiuchi, S. Murai. J. Am. Chem. Soc. 121, 8645 (1999). (http://dx.doi.org/10.1021/ja992048m)
• 9a. F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai. J. Am. Chem. Soc. 126, 2706 (2004). (http://dx.doi.org/10.1021/ja0393170)
• 9b. H. Tatamidani, K. Yokota, F. Kakiuchi, N. Chatani. J. Org. Chem. 69, 5615 (2004). (http://dx.doi.org/10.1021/jo0492719)
• 9c. Y. Harada, Y. Fukumoto, N. Chatani. Org. Lett. 7, 4385 (2005). (http://dx.doi.org/10.1021/ol0514956)
• 9d. J. Nakanishi, H. Tatamidani, Y. Fukumoto, N. Chatani. Synlett 869 (2006).
• 10a. S. Ueno, N. Chatani, F. Kakiuchi. J. Am. Chem. Soc. 129, 6098 (2007). (http://dx.doi.org/10.1021/ja0713431)
• 10b. T. Koreeda, T. Kochi, F. Kakiuchi. J. Am. Chem. Soc. 131, 7238 (2009). (http://dx.doi.org/10.1021/ja902829p)
• 11. S. Imoto, T. Uemura, F. Kakiuchi, N. Chatani. Synlett 170 (2007) and refs. cited therein.
• 12. K. Yokota, H. Tatamidani, Y. Fukumoto, N. Chatani. Org. Lett. 5, 4329 (2003). (http://dx.doi.org/10.1021/ol035582e)
• 13a. J. F. Knifton. J. Mol. Catal. 2, 293 (1977).
• 13b. Y. Tsuji, T. Kondo, Y. Watanabe. J. Mol. Catal. 40, 295 (1987).
• 13c. B. E. Ali, H. Alper. J. Mol. Catal. 67, 29 (1991).
• 13d. E. I. Drent, P. Arnoldy, P. H. M. Budzelaar. J. Organomet. Chem. 455, 247 (1993). (http://dx.doi.org/10.1016/0022-328X(93)80406-2)
• 13e. B. E. Ali, J. Tijani, A. M. El‑Ghanam. Tetrahedron Lett. 42, 2385 (2001).
• 13f. Y. Na, S. Ko, L. Hwang, S. Chang. Tetrahedron Lett. 44, 4475 (2003). (http://dx.doi.org/10.1016/S0040-4039(03)01016-5)
• 14a. B. El Ali, H. Alper. Synlett 161 (2000). (http://dx.doi.org/10.1055/s-2000-6477)
• 14b. T. F. Murray, J. R. Norton. J. Am. Chem. Soc. 101, 4107 (1979). (http://dx.doi.org/10.1021/ja00509a017)
• 14c. T. F. Murray, E. G. Samsel, V. Varma, J. R. Norton. J. Am. Chem. Soc. 103, 7520 (1981). (http://dx.doi.org/10.1021/ja00415a020)
• 14d. W. Y. Yu, H. Alper. J. Org. Chem. 62, 5684 (1997). (http://dx.doi.org/10.1021/jo9703663)
• 14e. C. S. Consorti, G. Ebeling, J. Dupont. Tetrahedron Lett. 43, 753 (2002). (http://dx.doi.org/10.1016/S0040-4039(01)02309-7)
• 15. S. Inoue, K. Yokota, H. Tatamidani, Y. Fukumoto, N. Chatani. Org. Lett. 8, 2519 (2006). (http://dx.doi.org/10.1021/ol060715s)
• 16. S. Inoue, Y. Fukumoto, N. Chatani. J. Org. Chem. 72, 6558 (2007).
• 17. For papers on η²-isocyanate complexes, see.
• 17a. G. La Monica, S. Cenini, M. Freni. J. Organomet. Chem. 76, 355 (1974). (http://dx.doi.org/10.1016/S0022-328X(00)87383-0)
• 17b. J. Drapier, M. T. Hoornaerts, A. J. Hubert, P. Teyssie. J. Mol. Catal. 11, 53 (1981).
• 17c. Isocyanates are well known to participate in cycloaddition reactions as two-atom components. For recent papers, see: Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiyama, K. Itoh. J. Am. Chem. Soc. 127, 605 (2005). (http://dx.doi.org/10.1021/ja045694g)
• 17d. L. V. R. Boñaga, H.-C. Zhang, A. F. Moretto, H. Ye, D. A. Li, J. Gauthier, G. C. Leo, B. E. Maryanoff. J. Am. Chem. Soc. 127, 3473 (2005). (http://dx.doi.org/10.1021/ja045001w)
• 17e. K. Tanaka, Y. Hagimura, M. Hirano. Angew. Chem., Int. Ed. 45, 2734 (2006). (http://dx.doi.org/10.1002/anie.200504470)
• 17f. R. T. Yu, T. Rovis. J. Am. Chem. Soc. 128, 14816 (2006).
• 18. T. Kondo, M. Momura, Y. Ura, K. Wada, T. Mitsudo. J. Am. Chem. Soc. 128, 14816 (2006). (http://dx.doi.org/10.1021/ja066305g)
• 19. For recent examples of carbonylation of alkynes with amines, see.
• 19a. Y. Li, H. Alper, Z. Yu. Org. Lett. 8, 5199 (2006). (http://dx.doi.org/10.1021/ol061675v)
• 19b. J. H. Park, S. Y. Kim, S. M. Kim, Y. K. Chung. Org. Lett. 9, 2465 (2007). (http://dx.doi.org/10.1021/ol0706760)
• 20. V. G. Zaitsev, D. Shabashov, O. Daugulis. J. Am. Chem. Soc. 127, 13154 (2005). (http://dx.doi.org/10.1021/ja054549f)
• 21. S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani. J. Am. Chem. Soc. 131, 6898 (2009). (http://dx.doi.org/10.1021/ja900046z)