Intramolecular carbostannylation of alkynes catalyzed by silver(I) species

Angewandte Chemie - International Edition

Volumn 46, Issue 15, 2007, Pages 2672-2676

  Porcel, Susana ^a,b   Echavarren, Antonio M ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Cyclization; Enantioselectivity; Enynes; Silver; Stannanes

Indexed keywords

CATALYST ACTIVITY; ISOMERS; REACTION KINETICS; SILVER; STEREOSELECTIVITY; TRANSITION METAL COMPOUNDS;

CARBOSTANNYLATION; ELECTROPHILIC TRANSITION-METAL COMPLEXES;

HYDROCARBONS;

EID: 34250832743     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605041     Document Type: Article

References (61)

1. For reviews, see: a) G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236;
2. b) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
3. c) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
4. d) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436;
5. e) E. Jimenez-Nunez, A. M. Echavarren, Chem. Commun. 2006, 333-346.
6. a) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222;
7. b) C. Fernández-Rivas, M. Méndez, C. Nieto-Oberhuber, A. M. Echavarren, J. Org. Chem. 2002, 67, 5197-5201.
8. M. Méndez, A. M. Echavarren, Eur. J. Org. Chem. 2002, 15-28.
9. a) B. Martín-Matute, E. Buñuel, D. J. Cárdenas, M. Méndez, C. Nieto-Oberhuber, A. M. Echavarren, J. Organomet. Chem. 2003, 687, 410-419;
10. b) S. Shin, T. V. RajanBabu, J. Am. Chem. Soc. 2001, 123, 8416-8417.
11. K. Miura, N. Fujisawa, H. Saito, H. Nishikori, A. Hosomi, Chem. Lett. 2002, 32-33.
12. K. Miura, N. Fujisawa, A. Hosomi, J. Org. Chem. 2004, 69, 2427-2430.
13. The intramolecular addition of allylsilanes to alkynes promoted by indium(III) takes place by a mechanism similar to that proposed in Ref. [2]. See: K. Miura, N. Fujisawa, S. Toyohara, A. Hosomi, Synlett 2006, 1883-1886.
14. 3 that involves a halogen transfer, see: G. R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048.
15. a) M. Méndez, M. P. Muñoz, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 11549-11550;
16. b) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520.
17. a) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
18. Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
19. b) C. Nieto-Oberhuber, M. P. Muñoz, S. López, E. Jimenez-Nunez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677-1693;
20. c)C. Nieto-Oberhuber, S. Lopez, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304;
21. Angew. Chem. Int. Ed. 2005, 44, 6146-6148;
22. d) C. Nieto-Oberhuber, S. López, E. Jiménez- Núñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923.
23. See, for example: a) D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260-11261;
24. b) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4526-4527;
25. c) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4526-4527;
26. d) B. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 15978-15979.
27. S. Ma, S. Yu, Z. Gu, Angew. Chem. 2006, 118, 206-209;
28. Angew. Chem. Int. Ed. 2006, 45, 200-203.
29. For leading references of silver(I)-catalyzed cyclizations of alkynes, see: a) R. F. Sweis, M. P. Schramm, S. A. Kozmin, J. Am. Chem. Soc. 2004 126, 7442-7443;
30. b) T. J. Harrison, G. R. Dake, Org. Lett. 2004, 6, 5023-5026;
31. c) T. J. Harrison, J. A. Kozak, M. Corbella-Pané, G. R. Dake, J. Org. Chem. 2006, 71, 4525-4529;
32. d) J. Sun, S. A. Kozmin, Angew. Chem. 2006, 118, 5113-5115;
33. Angew. Chem. Int. Ed. 2006, 45, 4991-4993;
34. e) J. Zhao, C. O. Hughes, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 7436-7437.
35. For leading references on silver(I)-carbene complexes, see: a) J. C. Garrison, W. J. Youngs, Chem. Rev. 2005, 105, 3978-4008;
36. b) P. de Frémont, N. M. Scott, E. D. Stevens, T. Ramnial, O. C. Lightbody, C. L. B. Macdonald, J. A. C. Clyburne, C. D. Abernethy, S. P. Nolan, Organometallics 2005, 24, 6301-6309;
37. c) R. R. Julian, J. A. May, B. M. Stoltz, J. L. Beauchamp, J. Am. Chem. Soc. 2003, 125, 4478-4486;
38. d) A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405-3409.
39. For discussions on π-back bonding in silver(I)-carbene complexes, see: a) X. Hu, I. Castro-Rodriguez, K. Olsen, K. Meyer, Organometallics 1993, 12, 3405-3409;
40. b) D. Nemcsok, K. Wichmann, G. Frenking, Organometallics 2004, 23, 3640-3646.
41. a) M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556-14557;
42. b) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5360-5361;
43. c) M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem. 2003, 68, 5593-5601;
44. d) A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723-4724.
45. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763-2793.
46. M. Bardají, O. Crespo, A. Laguna, A. K. Fischer, Inorg. Chim. Acta 2000, 304, 7-16.
47. S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt, J. Am. Chem. Soc. 2005, 127, 9976-9977.
48. a) E. Herrero-Gómez, C. Nieto-Oberhuber, S. López, J. Benet-Buchholz, A. M. Echavarren, Angew. Chem. 2006, 118, 5581-5585;
49. Angew. Chem. Int. Ed. 2006, 45, 5455-5459;
50. b) CCDC-634526 contains the supplementary crystallographic data for complex 8. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif..
51. C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
52. For details, see the Supporting Information.
53. a) S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. 2004, 116, 1152-1156;
54. Angew. Chem. Int. Ed. 2004, 43, 1132-1136;
55. b) S. P. H. Mee, V. Lee, J. E. Baldwin, Chem. Eur. J. 2005, 11, 3294-3308.
56. M. Yasuhisa, A. Naoki, K. Haruo, Yoshinori, Y. Tetrahedron 1999, 55, 3779-3790.
57. For enantioselective cyclizations of enynes initiated by the coordination of the metal to the alkyne function of enynes, see: platinum(III) catalysis: a) L. Charruault, V. Michelet, R. Taras, S. Gladialli, J.-P. Genêt, Chem. Commun. 2004, 850-851;
58. silver(I) catalysis: b) M. P. Mun̂oz, J. Adrio, J. C. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
59. a) U. Létinois-Halbes, P. Pale, S. Berger, J. Org. Chem. 2005, 70, 9185-9190;
60. b) A. Vitérisi, A. Orsini, J.-M. Weibel, P. Pal, Tetrahedron Lett. 2006, 47, 2779-2781, and references therein.
61. For closely related examples of intramolecular cyclopropanation reactions catalyzed by ruthenium(II) or platinum(II), see: B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524-9525.