Isolation of a zwitterionic dienegold(III) Complex intermediate in the direct conversion of enyne-amines to cyclopentadienes

Chemistry - A European Journal

Volumn 16, Issue 28, 2010, Pages 8262-8267

  Melchionna, Michele ^a   Nieger, Martin ^a   Helaja, Juho ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Alkynes; C h activation; Cyclopentadienes; Gold; Zwitterions

Indexed keywords

C-H ACTIVATION; CATALYZED CONVERSION; CYCLOPENTADIENES; DIRECT CONVERSION;

ACETYLENE; ACTIVATION ANALYSIS; GOLD COMPOUNDS; OLEFINS; ORGANIC COMPOUNDS;

GOLD;

EID: 77954835071     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000988     Document Type: Article

References (69)

1. Recent reviews on gold catalysis: a) A. S. K. Hashmi, Graham J. Hutchings, Angew. Chem. 2006, 118, 8064-8105;
2. Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
3. b) D.J. Gorin, F.D. Toste, Nature 2007, 446, 395-403;
4. c) A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
5. Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
6. d) Z. Li, C. Brouwer C. He, Chem. Rev. 2008, 108, 3239-3265;
7. e) A. Arcadi, Chem. Rev. 2008, 108, 3266-3325;
8. f) E. Jimenez-Nunez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350.
9. I-mediated catalysis: a) C. Nevado, A. M. Echavarren, Chem. Eur. J. 2005, 11, 3155-3164;
10. b) N. Marion, S. P. Nolan, Angew. Chem. 2007, 119, 2806-2809;
11. Angew. Chem. Int. Ed. 2007, 46, 2750-2752;
12. c) G. Seidel, R. Mynott, A. Furstner, Angew. Chem. 2009, 121, 2548-2551;
13. Angew. Chem. Int. Ed. 2009, 48, 2510-2513;
14. d) A. Gonzalèz Pérez, C.S. López, J. Marco-Contelles, O. N. Faza, E. Soriano, A. R. de Lera, J. Org. Chem. 2009, 74, 2982-2991;
15. 3 catalysis:
16. f) A.S.K. Hashmi, M. Rudolph, H.-U. Siehl, M. Tanaka, J. W. Bats, W. Frey, Chem Eur. J. 2008, 14, 3703-3708.
17. Selected reviews: a) K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263-3283;
18. b) S. E. Gibson (nèe Thomas), A. Stevenazzi, Angew. Chem. 2003, 115, 1844-1854;
19. Angew. Chem. Int. Ed. 2003, 42, 1800-1810;
20. c) H.-W. Lee, E-Y. Kwong, Eur. J. Org. Chem. 2010, 789-811.
21. Selected reviews: a) M. A. Tius, Eur. J. Org. Chem. 2005, 2193-2206;
22. b) H. Pellissier, Tetrahedron 2005, 61, 6479-6517;
23. c) A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577-7606.
24. J. H. Lee, F. D. Toste, Angew. Chem. 2007, 119, 930-932;
25. Angew. Chem. Int. Ed. 2007, 46, 912-914.
26. H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927-929;
27. Angew. Chem. Int. Ed. 2007, 46, 909-911.
28. V. K.-Y. Lo, M.-K. Wong, C.-M. Che, Org. Lett. 2008, 10, 517-519.
29. V. K.-Y. Lo, C.-Y. Zhou, M.-K. Wong, C.-M. Che, Chem. Commun. 2010, 46, 213-215.
30. Example of subtle substrate-dependent regioselectivity in propargylamide cycloisomerizations: N-propargyl carboxamides, having terminal alkynyl groups undergo 5-exo-dig cyclizations and N-alkynyl carbamates experience the 5-endo-dig cyclization, whereas different N-propargyl carboxamides having internal, alkyl-substituted C≡C triple bonds were converted to six-membered heterocycles;
31. a) A. S. K. Hashmi, R. Salath, W. Frey, Synlett 2007, 1763-1766;
32. b) A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394;
33. c) A. S. K. Hashmi, A. M. Schuster, F. Rominger, Angew. Chem. 2009, 121, 8396-8398;
34. I, respectively:
35. d) J. P. Weyrauch, A. S. K. Hashmi, A. Schuster, T. Hengst, S. Schetter, A. Littmann, M. Rudolph, M, Hamzic, J. Visus, F. Rominger, W. Frey, J. W. Bats, Chem. Eur. J. 2010, 16, 956-963.
36. III-catalyzed regiodependent cycloisomerizations of indole alkynes: a) C. Ferrer, A.M. Echavarren, Angew. Chem. 2006, 118, 1123-1127;
37. Angew. Chem. Int. Ed. 2006, 45, 1105-1109;
38. b) C. Ferrer, C.H.M. Amijs, A.M. Echavarren, Chem. Eur. J. 2007, 13, 1358-1373, and references therein.
39. A. S. K. Hashmi, J.P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. 2004, 116, 6707-6709;
40. Angew. Chem. Int. Ed. 2004, 43, 6545-6547.
41. a) T. J. Brown, M. G. Dickens, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 6350-6351;
42. b) M. A. Cinellu, G. Minghetti, S. Stoccoro, A. Zueca, M. Manassero, Chem. Commun. 2004, 1618-1619.
43. CCDC-767926 (7c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam ac.uk/data-request/cif. See experimental in the Supporting Information.
44. III is bridging tetraphenyldiene: a) M. Bois d'Enghien-Peteau, J. Meunier-Piret, M. van Meerssche, Cryst. Struct. Commun. 1975, 4, 375-381;
45. b) R. Usón, J. Vicente, M. T. Chicote, P. G. Jones, G. M. Sheldrick, J. Chem. Soc. Dalton Trans. 1983, 1131-1136.
46. I complexes: a) L.-P. Liu, B. Xu, M. S. Mashuta, G. B. Hammond, J. Am. Chem. Soc. 2008, 130, 17642-17643;
47. b) D. Weber, M. A. Tarselli, M. R. Gagné, Angew. Chem. 2009, 121, 5843-5846;
48. Angew. Chem. Int. Ed. 2009, 48, 5733-5736;
49. c) Y. Shi, S.D. Ramgren, S.A. Blum, Organometallics 2009, 28, 1275-1277;
50. d) X. Zeng, R. Kinjo, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 942-945;
51. 2-coordinated alkene:
52. f) N. D. Shapiro, F. D. Toste, Proc. Natl. Acad. Sci. USA 2008, 105, 2779-2782; cationic π-alkene complexes:
53. g) see ref [12a];
54. h) D. Zuccaccia, L. Belpassi, F. Tarantelli, A. Macchioni, J. Am. Chem. Soc. 2009, 131, 3170-3171;
55. I π-arene complexes:
56. j) E. Herrero-Gómez, C. Nieto-Oberhuber, S. López, J. Benet-Buchholz, A. M. Echavarren, Angew. Chem. 2006, 118, 5581-5585;
57. Angew. Chem. Int. Ed. 2006, 45, 5455-5459;
58. k) V. Lavallo, G. D. Frey, S. Kousar, B. Donnadieu, G. Bertrand, Proc. Natl. Acad. Sci. USA 2007, 104, 13569-13573;
59. I) V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2008, 120, 5302-5306;
60. Angew. Chem. Int. Ed. 2008, 47, 5224-5228.
61. 2(ligand): a) Y. Fuchita, Y. Utsunomiya, M. Yasutake, J. Chem. Soc. Dalton Trans. 2001, 2330-2334; heterocyclic cycloauric structures:
62. b) M. Nonoyama, K. Nakajima, K. Nonoyama, Polyhedron 1997, 16, 4039-4044;
63. c) Y. Fuchita, H. leda, Y. Tsunemune, J. Kinoshita-Nagaoka, H. Kawanoc, J. Chem. Soc. Dalton Trans. 1998, 791-796;
64. d) Y. Zhu, B. R. Cameron, R. T. Skerlj, J. Organomet. Chem. 2003, 677, 57-72;
65. e) D. Fan, C.-T. Yang, J. D. Ranford, P. Foo Lee, J. J. Vittal, Dalton Trans 2003, 2680-2685;
66. f) M. A. Cinellu, G. Minghetti, F. Coceo, S. Stoccoro, A. Zucca, M. Manassero Angew. Chem. 2005, 117, 7052;
67. Angew. Chem. Int. Ed. 2005, 44, 6892-6895.
68. Gaussian 03, Revision E.0l, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J.C Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
69. Recent relativistic comparison between Au- and Pt-mediated catalysis: M. Pernpointner, A. S. K. Hashmi, J. Chem. Theory Comput. 2009, 5, 2717-2725.