Abstract
Several reactions of simple, unactivated alkenes with electrophiles under Ni(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes act as the functional equivalents of alkenyl- and allylmetal reagents.
Conference
International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 14th, Nara, Japan, 2007-08-02–2007-08-06
References
1. G. R. Lappin, J. D. Sauer (Eds.). Alpha Olefins Applications Handbook, Marcel Dekker, New York (1989).Search in Google Scholar
2. doi:10.1021/ja9719182, E. Oblinger, J. Montgomery. J. Am. Chem. Soc. 119, 9065 (1997).Search in Google Scholar
3. doi:10.1021/ol006781q, W.-S. Huang, J. Chan, T. F. Jamison. Org Lett. 2, 4221 (2000).Search in Google Scholar
4. (a) doi:10.1021/ja034366y, K. M. Miller, W.-S. Huang, T. F. Jamison. J. Am. Chem. Soc. 125, 3442 (2003);Search in Google Scholar
4. (b) A. R. Van Dyke, K. M. Miller, T. F. Jamison. Org. Synth. 84, 111 (2007).Search in Google Scholar
5. doi:10.1021/ja072992f, M. R. Chaulagain, G. J. Sormunen, J. Montgomery. J. Am. Chem. Soc. 129, 9568 (2007).Search in Google Scholar
6. (a) doi:10.1021/ja0491735, K. M. Miller, T. Luanphaisarnnont, C. Molinaro, T. F. Jamison. J. Am. Chem. Soc. 126, 4130 (2004);Search in Google Scholar
6. (b) doi:10.1021/ja0446799, K. M. Miller, T. F. Jamison. J. Am. Chem. Soc. 126, 15342 (2004).Search in Google Scholar
7. doi:10.1021/ja0361401, C. Molinaro, T. F. Jamison. J. Am. Chem. Soc. 125, 8076 (2003).Search in Google Scholar
8. (a) doi:10.1002/anie.200390349, S. J. Patel, T. F. Jamison. Angew. Chem., Int. Ed. 42, 1364 (2003);Search in Google Scholar
8. (b) doi:10.1002/anie.200460044, S. J. Patel, T. F. Jamison. Angew. Chem., Int. Ed. 43, 3941 (2004).Search in Google Scholar
9. (a) doi:10.1002/anie.200300634, J. Montgomery. Angew. Chem., Int. Ed. 43, 3890 (2004);Search in Google Scholar
9. (b) J. Montgomery, G. J. Sormunen. Top. Curr. Chem. 279, 1 (2007);Search in Google Scholar
9. (c) doi:10.1039/b707737h, R. M. Moslin, K. Miller-Moslin, T. F. Jamison. Chem. Commun. 4441 (2007).Search in Google Scholar
10. (a) doi:10.1039/b001457p, U. Anwar, R. Grigg, M. Rasparini, V. Sridharan. Chem. Commun. 645 (2000);Search in Google Scholar
10. (b) doi:10.1021/ol025557t, Y.-H. Ha, S.-K. Kang. Org. Lett. 4, 1143 (2002);Search in Google Scholar
10. (c) doi:10.1021/ol0492795, C. D. Hopkins, H. C. Malinakova. Org. Lett. 6, 2221 (2004);Search in Google Scholar
10. (d) doi:10.1021/ol026670m, J. Montgomery, M. Song. Org. Lett. 4, 4009 (2002);Search in Google Scholar
10. (e) doi:10.1039/b207620a, S.-K. Kang, S.K. Yoon. Chem. Commun. 2634 (2002);Search in Google Scholar
10. (f) doi:10.1021/ja037718+, M.-S. Wu, D. K. Rayabarapu, C.-H. Cheng. J. Am. Chem. Soc. 125, 12426 (2003).Search in Google Scholar
11. (a) doi:10.1021/ja0521831, S.-S. Ng, T. F. Jamison. J. Am. Chem. Soc. 127, 7320 (2005);Search in Google Scholar
11. (b) doi:10.1016/j.tet.2005.08.063, S.-S. Ng, T. F. Jamison. Tetrahedron 61, 11405 (2006).Search in Google Scholar
12. (a) doi:10.1021/ja00130a021, N. M. Kablaoui, S. L. Buchwald. J. Am. Chem. Soc. 117, 6785 (1995);Search in Google Scholar
12. (b) doi:10.1021/ja00130a022, W. E. Crowe, M. J. Rachita. J. Am. Chem. Soc. 117, 6787 (1995).Search in Google Scholar
13. doi:10.1021/ja0460716, S. Ogoshi, M.-a. Oka, H. Kurosawa. J. Am. Chem. Soc. 126, 11802 (2004).Search in Google Scholar
14. doi:10.1021/ja0542486, S. Ogoshi, M. Ueta, T. Arai, H. Kurosawa. J. Am. Chem. Soc. 127, 12810 (2005).Search in Google Scholar
15. (a) doi:10.1002/cber.19430760105, K. Alder, F. Pascher, A. Schmitz. Ber. Dtsch. Chem. Ges. 76, 27 (1943);Search in Google Scholar
15. (b) B. B. Snider. In Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, I. Fleming (Eds.), p. 527, Pergamon Press, Oxford (1991).Search in Google Scholar
16. doi:10.1021/ja055363j, S.-S. Ng, T. F. Jamison. J. Am. Chem. Soc. 127, 14194 (2005).Search in Google Scholar
17. doi:10.1021/ja062866w, S.-S. Ng, C.-Y. Ho, T. F. Jamison. J. Am. Chem. Soc. 128, 11513 (2006).Search in Google Scholar
18. doi:10.1021/ja061471+, C.-Y. Ho, S.-S. Ng, T. F. Jamison. J. Am. Chem. Soc. 128, 5362 (2006).Search in Google Scholar
19. (a) E.-I. Negishi. Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley-Interscience, New York (2002);10.1002/0471473804Search in Google Scholar
19. (b) doi:10.1021/cr9903048, I. P. Beletskaya, A. V. Cheprakov. Chem. Rev. 100, 3009 (2000);Search in Google Scholar
19. (c) doi:10.1021/ja0471424, I. D. Hills, G. C. Fu. J. Am. Chem. Soc. 126, 13178 (2004).Search in Google Scholar
20. doi:10.1002/anie.200603907, C.-Y. Ho, T. F. Jamison. Angew. Chem., Int. Ed. 46, 782 (2007).Search in Google Scholar
21. doi:10.1021/cr020040g, T. V. Rajanbabu. Chem. Rev. 103, 2845 (2003).Search in Google Scholar
22. doi:10.1021/ja00743a009, T. Yamamoto, A. Yamamoto, S. Ikeda. J. Am. Chem. Soc. 93, 3350 (1971).Search in Google Scholar
23. (a) doi:10.1021/om50004a042, S. Komiya, Y. Abe, A. Yamamoto, T. Yamamoto. Organometallics 2, 1466 (1983);Search in Google Scholar
23. (b) doi:10.1021/ol049908a, R. Sawaki, Y. Sato, M. Mori. Org. Lett. 6, 1131 (2004).Search in Google Scholar
24. H. Hoberg, K. Summermann, A. Milchereit. Angew. Chem., Int. Ed. Engl. 24, 325 (1985).Search in Google Scholar
25. doi:10.1039/c39860000544, H. Hoberg, E. Hernandez. J. Chem. Soc., Chem. Commun. 544 (1986).Search in Google Scholar
26. H. Hoberg. J. Organomet. Chem. 358, 507 (1988) and refs. cited therein.10.1016/0022-328X(88)87099-2Search in Google Scholar
27. doi:10.1021/ol063111x, K. D. Schleicher, T. F. Jamison. Org. Lett. 9, 875 (2007).Search in Google Scholar
28. doi:10.1021/ol048211m, H. A. Duong, M. J. Cross, J. Louie. Org. Lett. 6, 4679 (2004).Search in Google Scholar
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