Synthesis of N-aryl-2-allylpyrrolidines via palladium-catalyzed carboamination reactions of γ-(N-arylamino)alkenes with vinyl bromides

Advanced Synthesis and Catalysis

Volumn 347, Issue 11-13, 2005, Pages 1614-1620

  Ney, Joshua E ^a   Hay, Michael B ^a   Yang, Qifei ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Heterocycles; Homogeneous catalysis; Palladium; Pyrrolidines; Tandem reactions; Vinyl halides

Indexed keywords

EID: 27544515010     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505172     Document Type: Article

References (43)

1. a) G. Massiot, C. Delaude, Alkaloids 1986, 27, 269-322;
2. b) D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446;
3. c) J. R. Lewis, Nat. Prod. Rep. 2001, 18, 95-128.
4. a) M. Pichon, B. Figadere, Tetrahedron: Asymmetry 1996, 7, 927-964;
5. b) A. Mitchinson, A. Nadin, J. Chem. Soc. Perkin Trans. 1 2000, 2862-2892.
6. a) G. D. Harris, Jr., R. J. Herr, S. M. Weinreb, J. Org. Chem. 1992, 57, 2528-2530;
7. b) R. C. Larock, H. Yang, S. M. Weinreb, R. J. Herr, J. Org. Chem. 1994, 59, 4172-4178.
8. a) Y. Tamaru, M. Kimura, Synlett 1997, 749-757;
9. b) Y. Tamaru, M. Hojo, H. Higashimura, Z.-i. Yoshida, J. Am. Chem. Soc. 1988, 110, 3994-4002;
10. c) Y. Tamaru, M. Hojo, Z.-i. Yoshida, J. Org. Chem. 1988, 53, 5731-5741;
11. d) H. Harayama, A. Abe, T. Sakado, M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1997, 62, 2113-2122.
12. P. A. Jacobi, H. Liu, Org. Lett. 1999, 1, 341-344.
13. a) J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689-3692;
14. Angew. Chem. Int. Ed. 2004, 43, 3605-3608;
15. b) J. E. Ney, J. P. Wolfe, J. Am. Chem. Soc. 2005, 127, 8644-8651.
16. For a related synthesis of N-acyl- and N-boc-2-benzylpyrrolidines, see: M. B. Bertrand, J. P. Wolfe, Tetrahedron 2005, 61, 6447-6459.
17. For a related synthesis of tetrahydrofurans, see: a) J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc. 2004, 126, 1620-1621;
18. b) M. B. Hay, A. R. Hardin, J. P. Wolfe, J. Org. Chem. 2005, 70, 3099-3107.
19. 2, see: E. S. Sherman, S. R. Chemler, T. B. Tan, O. Gerlits, Org. Lett. 2004, 6, 1573-1575.
20. [6b]
21. and for a discussion of ligand effects on the rate of carbon-nitrogen bond-forming reductive elimination, see: b) B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 3694-3703;
22. c) for a discussion of ligand effects on the rate of carbon-carbon bond-forming reductive elimination, see: A. Gillie, J. K. Stille, J. Am. Chem. Soc. 1980, 102, 4933-4941.
23. For recent reports of palladium-catalyzed N-vinylation reactions, see: a) J. R. Dehli, J. Legros, C. Bolm, Chem. Commun. 2005, 973-986 and references cited therein;
24. b) J. Barluenga, M. A. Fernandez, F. Aznar, C. Valdes, Chem. Eur. J. 2004, 10, 494-507.
25. Pyrrolidines 3b and 3 h were obtained with > 20:1 E/Z ratios even though they were derived from geometrically impure vinyl bromides 2b and 2 h. These vinyl bromides were present in excess, and (E)-vinyl bromides have been shown to undergo oxidative addition faster than the corresponding (Z)-vinyl bromides; see: A. Jutand, S. Negri, Organometallics 2003, 22, 4229-4237.
26. Q. Yang, J. E. Ney, J. P. Wolfe, Org Lett. 2005, 7, 2575-2578.
27. R. Lira, J. P. Wolfe, J. Am. Chem. Soc. 2004, 126, 13906-13907.
28. For recent reviews on palladium-catalyzed N-arylation reactions, see: a) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131-209;
29. b) J. F. Hartwig, in: Modern Arene Chemistry, (Ed: D. Astruc), Wiley-VCH: Weinheim, 2002, pp. 107-168;
30. c) B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599-1626.
31. [11b]
32. For reports of rearranged products in palladium-catalyzed coupling reactions of (1-bromovinyl)trimethylsilane (2i), see: a) B. Cazes, V. Colovray, J. Gore, Tetrahedron Lett. 1988, 29, 627-630;
33. b) A. Carpita, R. Rossi, B. Scamuzzi, Tetrahedron Lett. 1989, 30, 2699-2702;
34. c) D. S. Ennis, T. L. Gilchrist, Tetrahedron 1990, 46, 2623-2632;
35. d) P. K. Sasmal, M. E. Maier, Org. Lett. 2002, 4, 1271-1274.
36. To the best of our knowledge, the formation of a side product analogous to 5 in a palladium-catalyzed coupling reaction of an E-substituted 1-bromo-1-alkene has been reported only once, see: E. M. Flamme, W. R. Roush, Org. Lett. 2005, 7, 1411-1414.
37. This reinsertion step fundamentally involves the hydropalladation of an alkyne; for examples of other reactions involving alkyne hydropalladation, see: a) V. V. Grushin, Chem. Rev. 1996, 96, 2011-2034 and references cited therein;
38. b) B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42;
39. c) J. Ji, Z. Wang, X. Lu, Organometallics 1996, 15, 2821-2828;
40. d) I. Kadota, L. M. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210.
41. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066 and references cited therein.
42. β-Hydride elimination reactions have been shown to involve the build up of positive charge at the β-carbon atom in the transition state; see: a) J. A. Mueller, C. P. Goller, M. S. Sigman, J. Am. Chem. Soc. 2004, 126, 9724-9734;
43. b) J. A. Mueller, M. S. Sigman, J. Am. Chem. Soc. 2003, 125, 7005-7013.