Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1089-1096
http://dx.doi.org/10.1351/pac200880051089
First palladium- and nickel-catalyzed oxidative diamination of alkenes: Cyclic urea, sulfamide, and guanidine building blocks
References
- 1. (a). D. Lucet, T. Le Gall, C. Mioskowski. Angew. Chem., Int. Ed. 37, 2580 (1998); (http://dx.doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L)
- 1. (b). Y. L. Bennani, S. Hanessian. Chem. Rev. 97, 3161 (1997). (http://dx.doi.org/10.1021/cr9407577)
- 2. (a). R. Noyori. Angew. Chem., Int. Ed. 41, 2008 (2002); (http://dx.doi.org/10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO;2-4)
- 2. (b). R. Noyori. Adv. Synth. Catal. 345, 15 (2003); (http://dx.doi.org/10.1002/adsc.200390002)
- 2. (c). R. Noyori, T. Ohkuma. Angew. Chem., Int. Ed. 40, 40 (2001); (http://dx.doi.org/10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5)
- 2. (d). R. Noyori, M. Yamakawa, S. Hashiguchi. J. Org. Chem. 66, 7931 (2001); (http://dx.doi.org/10.1021/jo010721w)
- 2. (e). R. Noyori, S. Hachiguchi. Acc. Chem. Res. 30, 97 (1997). (http://dx.doi.org/10.1021/ar9502341)
- 3. (a). K. Muniz. New J. Chem. 29, 1371 (2005); (http://dx.doi.org/10.1039/b506221g)
- 3. (b). K. Muniz. Chem. Soc. Rev. 33, 166 (2004); (http://dx.doi.org/10.1039/b307102m)
- 3. (c). A. O. Chong, K. Oshima, K. B. Sharpless. J. Am. Chem. Soc. 99, 3420 (1977); (http://dx.doi.org/10.1021/ja00452a039)
- 3. (d). J. T. Anhaus, T. P. Kee, M. H. Schofield, R. R. Schrock. J. Am. Chem. Soc. 112, 1642 (1990); (http://dx.doi.org/10.1021/ja00160a061)
- 3. (e). M. H. Schofield, T. P. Kee, J. T. Anhaus, R. R. Schrock, K. H. Johnson, W. M. Davis. Inorg. Chem. 30, 3595 (1991). (http://dx.doi.org/10.1021/ic00019a006)
- 4. (a). K. Muniz, M. Nieger. Synlett 211 (2003); (http://dx.doi.org/10.1055/s-2003-36799)
- 4. (b). K. Muniz, A. Iesato, M. Nieger. Chem.Eur. J. 9, 5581 (2003). (http://dx.doi.org/10.1002/chem.200305011)
- 5. (a). K. Muniz, M. Nieger. Chem. Commun. 2729 (2005); (http://dx.doi.org/10.1039/b502150b)
- 5. (b). I. Almodovar, C. H. Hovelmann, J. Streuff, M. Nieger, K. Muniz. Eur. J. Org. Chem. 704 (2006). (http://dx.doi.org/10.1002/ejoc.200500641)
- 6. K. Muniz, M. Nieger, H. Mansikkamaki. Angew. Chem., Int. Ed. 42, 5958 (2003). (http://dx.doi.org/10.1002/anie.200352244)
- 7. (a). V. Gomez Aranda, J. Barluenga, F. Aznar. Synthesis 504 (1974); (http://dx.doi.org/10.1055/s-1974-23358)
- 7. (b). J. Barluenga, L. Alonso-Cires, G. Asensio. Synthesis 962 (1979); (http://dx.doi.org/10.1055/s-1979-28890)
- 7. (c). J. Barluenga, F. Aznar, M. C. S. de Mattos, W. B. Kover, S. Garcia-Granda, E. Perez-Carreno. J. Org. Chem. 56, 2930 (1991); (http://dx.doi.org/10.1021/jo00008a066)
- 7. (d). J.-E. Backvall. Tetrahedron Lett. 16, 2225 (1975); (http://dx.doi.org/10.1016/S0040-4039(00)72683-9)
- 7. (e). J.-E. Backvall. Tetrahedron Lett. 19, 163 (1978); (http://dx.doi.org/10.1016/S0040-4039(01)85073-5)
- 7. (f). T. P. Zabawa, D. Kasi, S. R. Chemler. J. Am. Chem. Soc. 127, 11250 (2005); (http://dx.doi.org/10.1021/ja053335v)
- 7. (g). T. P. Zabawa, S. R. Chemler. Org. Lett. 9, 2035 (2007).
- 8. A. Minatti, K. Muniz. Chem. Soc. Rev. 36, 1142 (2007). (http://dx.doi.org/10.1039/b607474j)
- 9. J. Streuff, C. H. Hovelmann, M. Nieger, K. Muniz. J. Am. Chem. Soc. 127, 14587 (2005). (http://dx.doi.org/10.1021/ja055190y)
- 10. K. Muniz, M. Nieger. Synlett 149 (2005). (http://dx.doi.org/10.1055/s-2004-836052)
- 11. L. Alcaraz, C. Bennion, J. Morris, P. Meghani, S. M. Thom. Org. Lett. 6, 2705 (2004). (http://dx.doi.org/10.1021/ol049091l)
- 12. S. Cerezo, J. Cortes, M. Moreno-Manas, R. Pleixats, A. Roglans. Tetrahedron 54, 14869 (1998). (http://dx.doi.org/10.1016/S0040-4020(98)00930-2)
- 13. E. J. Alexanian, C. Lee, E. J. Sorensen. J. Am. Chem. Soc. 127, 7690 (2005). (http://dx.doi.org/10.1021/ja051406k)
- 14. K. Muniz, J. Steuff, C. H. Hovelmann, A. Nunez. Angew. Chem., Int. Ed. 46, 7125 (2007). (http://dx.doi.org/10.1002/anie.200702160)
- 15. (a). K. C. Nicolaou, D. A. Langbottom, S. A. Snyder, A. Z. Nalbandian, X. H. Huang. Angew. Chem., Int. Ed. 41, 3866 (2002); (http://dx.doi.org/10.1002/1521-3773(20021018)41:20<3866::AID-ANIE3866>3.0.CO;2-T)
- 15. (b). K. C. Nicolaou, S. A. Snyder, D. A. Langbottom, A. Z. Nalbandian, X. H. Huang. Chem.Eur. J. 10, 5581 (2004). (http://dx.doi.org/10.1002/chem.200400503)
- 16. K. Muniz and coworkers, unpublished results 2005-2007.
- 17. T. Yoneyama, R. H. Crabtree. J. Mol. Catal. A 108, 96 (1996).
- 18. (a). A. J. Canty. Acc. Chem. Res. 25, 83 (1992); (http://dx.doi.org/10.1021/ar00014a005)
- 18. (b). A. R. Dick, J. W. Kampf, M. S. Sanford. J. Am. Chem. Soc. 127, 12790 (2005); (http://dx.doi.org/10.1021/ja0541940)
- 18. (c). A. R. Dick, J. W. Kampf, M. S. Sanford. Organometallics 24, 482 (2005); (http://dx.doi.org/10.1021/om049163c)
- 18. (d). A. R. Dick, M. S. Sanford. Tetrahedron 62, 2439 (2006); (http://dx.doi.org/10.1016/j.tet.2005.11.027)
- 18. (e). A. J. Canty, M. C. Denney, B. W. Skelton, A. H. White. Organometallics 23, 1122 (2004); (http://dx.doi.org/10.1021/om030644q)
- 18. (f). A. J. Canty, M. C. Denney, G. van Koten, B. W. Skelton, A. H. White. Organometallics 23, 5432 (2004); (http://dx.doi.org/10.1021/om040061w)
- 18. (g). A. J. Canty, H. Jin, B. W. Skelton, A. H. White. Inorg. Chem. 37, 3975 (1998). (http://dx.doi.org/10.1021/ic9715005)
- 19. (a). B. L. Lin, C. R. Clough, G. L. Hillhouse. J. Am. Chem. Soc. 124, 2890 (2002); (http://dx.doi.org/10.1021/ja017652n)
- 19. (b). K. Koo, G. L. Hillhouse. Organometallics 14, 4421 (1995); (http://dx.doi.org/10.1021/om00009a054)
- 19. (c). K. Koo, G. L. Hillhouse. Organometallics 15, 2669 (1996). (http://dx.doi.org/10.1021/om960286+)
- 20. J. L. Brice, J. E. Harang, V. I. Timokhim, N. A. Anastasi, S. S. Stahl. J. Am. Chem. Soc. 127, 2868 (2005). (http://dx.doi.org/10.1021/ja0433020)
- 21. C-N bond formation from Pt(IV): A. V. Pawlikowski, A. D. Getty, K. I. Goldberg. J. Am. Chem. Soc. 129, 10382 (2007). (http://dx.doi.org/10.1021/ja069191h)
- 22. (a). A. R. Murci, S. L. Buchwald. Top. Curr. Chem. 219, 133 (2002);
- 22. (b). J. F. Hartwig. Angew. Chem., Int. Ed. 37, 2046 (1998); (http://dx.doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L)
- 22. (c). J. F. Hartwig. Inorg. Chem. 46, 1936 (2007); (http://dx.doi.org/10.1021/ic061926w)
- 22. (d). J. F. Hartwig. Acc. Chem. Res. 31, 852 (1998); (http://dx.doi.org/10.1021/ar970282g)
- 22. (e). J. Barluenga, C. Valdes. Chem. Commun. 4891 (2005). (http://dx.doi.org/10.1039/b509311b)
- 23. (a). G. L. J. Bar, G. C. Lloyd-Jones, K. I. Booker-Milburn. J. Am. Chem. Soc. 127, 7308 (2005); (http://dx.doi.org/10.1021/ja051181d)
- 23. (b). H. Du, B. Zhao, Y. Shi. J. Am. Chem. Soc. 129, 762 (2007); (http://dx.doi.org/10.1021/ja0680562)
- 23. (c). H. Du, W. Yuan, B. Zhao, Y. Shi. J. Am. Chem. Soc. 129, 7496 (2007); (http://dx.doi.org/10.1021/ja072080d)
- 23. (d). W. Yuan, H. Du, B. Zhao, Y. Shi. Org. Lett. 8, 2689 (2007).