Tandem catalysis: Generating multiple contiguous carbon-carbon bonds through a ruthenium-catalyzed ring-closing metathesis/Kharasch addition

Journal of the American Chemical Society

Volumn 127, Issue 46, 2005, Pages 16329-16332

  Seigal, Benjamin A ^a   Fajardo, Cristina ^a,b   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEX PRODUCTS; METATHESIS; REACTION VESSEL; TANDEM CATALYSIS;

APPROXIMATION THEORY; CATALYSIS; CHEMICAL BONDS; FUNCTIONS; MATHEMATICAL TRANSFORMATIONS; REACTION KINETICS; RUTHENIUM;

CARBON;

CARBON; RUTHENIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; MOLECULAR MECHANICS; MOLECULAR MODEL; RING CLOSING METATHESIS; STEREOCHEMISTRY; TANDEM CATALYSIS; TANDEM MASS SPECTROMETRY;

EID: 28044463154     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055806j     Document Type: Article

References (70)

1. While efforts are being made to define differences between tandem, domino, cascade, concurrent, and sequential catalytic processes, these terms are used interchangeably in this article without bias for the mechanistic implications of their emerging definitions. See ref 2b-d and Tietze, L. F.; Rackelmann, N. Pure App. Chem. 2004, 76, 1967 for additional discussions.
2. For reviews on tandem/domino catalysis, see: (a) De Meijere, A.; von Zezschwitz, P.; Bräse, S. Acc. Chem, Res. 2005, 38, 413.
3. (b) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
4. (c) Ajamian, A.; Gleason, J. L. Angew. Chem. Int. Ed. 2004, 43, 3754.
5. (d) Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365.
6. (e) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302.
7. (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227-255.
8. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237-1256.
9. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193-202.
10. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-165.
11. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167-176.
12. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206.
13. (l) Tietze, L. F. Chem. Rev. 1996, 96, 115.
14. (m) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159.
15. (n) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
16. For recent examples of tandem processes, see: (o) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305-3308.
17. (p) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459-3463.
18. (q) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719-1729.
19. (r) Vosburg, D. A.; Vanderwal, C. D.; Sorensen. E. J. J. Am. Chem. Soc. 2002, 124, 4552-4553.
20. (s) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294-295.
21. (t) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 11152.
22. (u) Breit, B.; Zahn, S. K. Angew. Chem. Int. Ed. 2001, 40, 1910.
23. Breit, B.; Zahn, S. K. Angew. Chem. Int. Ed. 1999, 38, 969.
24. For recent examples, see: (a) Guo, R.; Morris, R. H.; Song, D. J. Am. Chem. Soc. 2005, 127, 516.
25. (b) Ackermann, L. Org. Lett. 2005, 7, 439.
26. Ashfeld, B. L.; Miller, K. A.; Smith, A. J.; Tran, K.; Martin, S. F. Org. Lett. 2005, 7, 1661.
27. For recent reviews on olefin metatheses, see: (a) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
28. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
29. (a) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390-13391.
30. (b) Schmidt, B. Eur. J. Org. Chem. 2003, 816-819.
31. (c) Schmidt, B. Chem. Commun. 2004, 742-743.
32. (d) Schmidt, B. J. Org. Chem. 2004, 69, 7672-7687.
33. (a) Drouin, S.; Zamanian, F. Fogg, D. Organometallics 2001, 20, 5495.
34. (b) Schmidt, B.; Pohler, M. Org. Biomol. Chem. 2003, 1, 2512.
35. (a) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344-345.
36. (b) Simal, F.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 1999, 40, 5689-5693.
37. (c) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872.
38. Quayle, P.; Fengas, D.; Richards, S. Synlet 2003, 1797.
39. (e) Schmidt, B.; Pohler, M.; Costisella, B. J. Org. Chem. 2004, 69, 1421.
40. (f) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhung, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391-7396-345.
41. (a) Maifeld S. V.; Miller R.; Lee D. Tetrahedron Lett. 2002, 36, 6363-6365.
42. In addition, see: (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196-3201.
43. For a recent review of nonmetathetic reactions of Grubbs' catalyst, see: (c) Alcaide, B.; Almendros, P. Chem. Eur. J. 2003, 9, 1258.
44. For an overview of ruthenium-catalyzed reactions, see: (d) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660.
45. (e) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
46. (f) De Clercq, B.; Verpoort, F. Tetrahedron Lett. 2001, 42, 8959.
47. Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
48. For an overview of ruthenium-catalyzed reactions, see: (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660.
49. (b) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev., 2001, 101, 2067-2096.
50. (a) Kharasch, M. S.; Jensen, E. V.; Urry, U. H. Science 1945, 102, 128.
51. (b) DeMaldè, M.; Minisci, F. Pallini, U.; Volterra, E.; Quilico, A. Chim. Ind. (Milan) 1956, 38, 371.
52. (c) Asscher, M.; Vofsi, D. J. Chem. Soc. 1963, 1887-1896.
53. (d) De Clercq, B.; Verpoort, F. Tetrahedron Lett. 2002, 43, 4687-4690 and references therein.
54. (e) Matsumoto, H.; Nakano, T.; Nagai, Y. Tetrahedron Lett. 1973, 14, 5065-5150.
55. (f) Mori, Y.; Tsuji, J. Tetrahedron 1972, 28, 29-35.
56. (g) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281.
57. For recent ruthenium-catalyzed examples, see: (h) Quebatte, L.; Solari, E.; Scopelliti, R.; Severin, K. Organometallics 2005, 24, 1404.
58. (i) Delaude, L.; Demonceau, A.; Noels, A. F. Top. Organomet. Chem. 2004, 11, 155.
59. (j) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Vinas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421.
60. (k) Tutusaus, O.; Vinas, C.; Nunez, R., Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830.
61. (l) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11.
62. Preliminary screening efforts indicated that Grubbs' alkylidene 1 was more effective in catalyzing the Kharasch addition than the second-generation catalyst 2.
63. (a) Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901
64. (b) Donohoe, T. J.; Mitchell, L.; Waring, M. J.; Helliwell, M.; Bell, A.; Newcombe, N. J. Org. Biomol. Chem. 2003, 1, 2173.
65. For example, see: Anderson, C. E.; Donde, Y.; Douglas, C. J.; Overman, L. E. J. Org. Chem. 2005, 70, 648 and references therein.
66. Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281.
67. Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, T.; Watanabe, M.; Tajima, T.; Itoh, K. J. Org. Chem. 1992, 57, 1682.
68. Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391-7396-345.
69. Kleschick, W. A.; Reed, M. W.; Bordner, J. J. Org. Chem. 1987, 3168.
70. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J Organometallics 1996, 15, 1518.