Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1537-1544
http://dx.doi.org/10.1351/PAC-CON-09-10-18
Published online 2010-05-04
Alkynes as “masked” ylides under noble‑metal catalysis
References
- 1. 1,2-sigmatropic rearrangement of sulfonium ylides: T. J. Chem. Soc. 69 (1932). ( , T. S. Stevens. http://dx.doi.org/10.1039/jr9320000069)
- 2. 2,3-sigmatropic rearrangement of sulfonium ylides.
- 2a. G. M. Chem. Commun. 186 (1968). , W. D. Ollis, J. D. Plackett, C. Smith, I. O. Sutherland.
- 2b. J. E. Chem. Commun. 537 (1968). , R. E. Hackler, D. P. Kell.
- 2c. R. B. Tetrahedron Lett. 417 (1968). ( , D. Feld. http://dx.doi.org/10.1016/S0040-4039(01)98775-1)
- 2d. B. M. Tetrahedron Lett. 3327 (1968). ( , R. LaRochelle. http://dx.doi.org/10.1016/S0040-4039(00)89558-1)
- 3a. J. S. Clark. Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry, Oxford University Press, Oxford (2002).
- 3b. “Sulfur mediated rearrangements” in Topics in Current Chemistry, E. Schaumann (Ed.), Vol. 275, Springer, Heidelberg (2007).
- 4. M. P. Doyle, M. A. McKervey, T. Ye. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York (1998).
- 5. In situ decomposition of tosyl hydrazone salts avoids direct use of dangerous diazo compounds, although there is still a requirement for ornate functionality to be introduced immediately prior to the reaction, see: V. K. Acc. Chem. Res. 37, 611 (2004) and refs. therein. ( , C. L. Winn. http://dx.doi.org/10.1021/ar030045f)
- 6. P. W. Angew. Chem., Int. Ed. 48, 8372 (2009). ( , S. J.-C. Albrecht. http://dx.doi.org/10.1002/anie.200904309)
- 7. For selected reviews of gold and platinum catalysis.
- 7a. D. J. Chem. Rev. 108, 3351 (2008). ( , B. D. Sherry, F. D. Toste. http://dx.doi.org/10.1021/cr068430g)
- 7b. E. Chem. Rev. 108, 3326 (2008). ( , A. M. Echavarren. http://dx.doi.org/10.1021/cr0684319)
- 7c. J. Chem. Rev. 108, 3239 (2008). ( , C. Brouwer, C. He. http://dx.doi.org/10.1021/cr068434l)
- 7d. A. Chem. Rev. 108, 3266 (2008). ( . http://dx.doi.org/10.1021/cr068435d)
- 7e. H. C. Tetrahedron 64, 3885 (2008). ( . http://dx.doi.org/10.1016/j.tet.2008.01.081)
- 7f. H. C. Tetrahedron 64, 7847 (2008). ( . http://dx.doi.org/10.1016/j.tet.2008.05.082)
- 7g. A. S. K. Chem. Soc. Rev. 37, 1766 (2008). ( . http://dx.doi.org/10.1039/b615629k)
- 7h. A. S. K. Chem. Rev. 107, 3180 (2007). ( . http://dx.doi.org/10.1021/cr000436x)
- 7i. D. J. Nature 446, 395 (2007). ( , F. D. Toste. http://dx.doi.org/10.1038/nature05592)
- 7j. A. Angew. Chem., Int. Ed. 46, 3410 (2007). ( , P. W. Davies. http://dx.doi.org/10.1002/anie.200604335)
- 8. Y. Org. Lett. 5, 2619 (2003). ( , K. Miki, F. Nishino, K. Ohe, S. Uemura. http://dx.doi.org/10.1021/ol034731q)
- 9a. W. Chem. Ber. 101, 994 (1968). ( , M. Kapps. http://dx.doi.org/10.1002/cber.19681010333)
- 9b. M. P. J. Org. Chem. 49, 1917 (1984). ( , J. H. Griffin, M. S. Chinn, D. van Leusen. http://dx.doi.org/10.1021/jo00185a014)
- 9c. M. Reggelin. In Sulfur-Mediated Rearrangements II, Topics in Current Chemistry, 275, pp. 1–65, Springer (2007).
- 10. Selected reviews.
- 10a. N. Angew. Chem., Int. Ed. 46, 2750 (2007). ( , S. P. Nolan. http://dx.doi.org/10.1002/anie.200604773)
- 10b. J. Chem.—Eur. J. 13, 1350 (2007). ( , E. Soriano. http://dx.doi.org/10.1002/chem.200601522)
- 11. Selected intermolecular examples.
- 11a. cationic gold complexes: M. J. J. Am. Chem. Soc. 127, 18002 (2005). ( , D. J. Gorin, S. T. Staben, F. D. Toste. http://dx.doi.org/10.1021/ja0552500)
- 11b. Pt catalysis: K. Org. Lett. 8, 1741 (2006). ( , M. Fujita, S. Uemura, K. Ohe. http://dx.doi.org/10.1021/ol0604769)
- 12. P. W. Chem. Commun. 238 (2008). ( , S. J.-C. Albrecht. http://dx.doi.org/10.1039/b714813e)
- 13a. R. J. Org. Chem. 66, 5256 (2001). ( , D. L. Van Vranken. http://dx.doi.org/10.1021/jo010247u)
- 13b. M. E. Org. Lett. 1, 367 (1999). ( , J. Pontillo. http://dx.doi.org/10.1021/ol9900257)
- 13c. F. Bull. Chem. Soc. Jpn. 65, 2471 (1992). ( , T. Abiko, M. Kato. http://dx.doi.org/10.1246/bcsj.65.2471)
- 13d. M. P. J. Chem. Soc., Chem. Commun. 46 (1990). ( , V. Bagheri, E. E. Claxton. http://dx.doi.org/10.1039/c39900000046)
- 13e. P. A. J. Org. Chem. 39, 119 (1974). ( , M. Meyers, R. S. Finkelhor. http://dx.doi.org/10.1021/jo00915a035)
- 13f. G. Bull. Chem. Soc. Fr. 1281 (1975). , L. Veniard, P. Cadiot.
- 14. Representative examples of silver-catalyzed atom-transfer reactions.
- 14a. S. Org. Biomol. Chem. 2, 3044 (2004). ( , D. Fielenbach, K. A. Jorgenson. http://dx.doi.org/10.1039/b412053a)
- 14b. P. Chem. Commun. 731 (2007). ( , R. G. Browning, S. Singh, R. Sivappa, C. J. Lovely, H. V. R. Dias. http://dx.doi.org/10.1039/b608266a)
- 14c. J. L. J. Am. Chem. Soc. 129, 6090 (2007). ( , H. M. L. Davies. http://dx.doi.org/10.1021/ja069314y)
- 14d. H. Angew. Chem., Int. Ed. 47, 8933 (2008). ( , W. Zhang, D. Shu, J. B. Werness, W. Tang. http://dx.doi.org/10.1002/anie.200803910)
- 15. P. W. Org. Biomol. Chem. 7, 1276 (2009). ( , S. J.-C. Albrecht, G. Assanelli. http://dx.doi.org/10.1039/b822584b)
- 16a. I. Angew. Chem., Int. Ed. 45, 4473 (2006). ( , T. Sato, Y. Yamamoto. http://dx.doi.org/10.1002/anie.200601178)
- 16b. I. Org. Lett. 10, 2649 (2008). ( , T. Sato, M. Terada, Y. Yamamoto. http://dx.doi.org/10.1021/ol8007556)
- 17a. N. D. J. Am. Chem. Soc. 129, 4160 (2007). ( , F. D. Toste. http://dx.doi.org/10.1021/ja070789e)
- 17b. G. Angew. Chem., Int. Ed. 46, 5156 (2007). ( , L. Zhang. http://dx.doi.org/10.1002/anie.200701449)
- 18. H.-S. Angew. Chem., Int. Ed. 47, 7040 (2008). ( , J.-E. Lee, S. Shin. http://dx.doi.org/10.1002/anie.200802802)