Gold for the generation and control of fluxional barbaralyl cations

Angewandte Chemie - International Edition

Volumn 51, Issue 52, 2012, Pages 13093-13096

  McGonigal, Paul R ^a   De León, Claudia ^a   Wang, Yahui ^a   Homs, Anna ^a   Solorio Alvarado, César R ^a   Echavarren, Antonio M ^a,b  

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

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Barbaralyl cations; Cyclization; Enynes; Fluxionality; Gold catalysis

Indexed keywords

ACIDIC MEDIA; AMBIENT CONDITIONS; CARBON ATOMS; CARBON SKELETON; ENYNES; FLUXIONALITY; FUNCTIONALIZED; GOLD CATALYSIS; MOLECULAR TRANSPORT; MULTI-STEP; PERICYCLIC REACTION; REACTION CONDITIONS; SEMIBULLVALENE; SINGLE MOLECULE; SWITCHABLE;

CARBON; CYCLIZATION; GOLD; HYDROCARBONS; ISOMERS; MOLECULES;

POSITIVE IONS;

EID: 84871981789     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207682     Document Type: Article

References (51)

1. W. von E. Doering, W. R. Roth, Tetrahedron 1963, 19, 715-737
2. G. Schrçder, Angew. Chem. 1963, 75, 722
3. Angew. Chem. Int. Ed. Engl. 1963, 2, 481-482.
4. R. V. Williams, Chem. Rev. 2001, 101, 1185-1204
5. M. He, J. W. Bode, Proc. Natl. Acad. Sci. USA 2011, 108, 14752-14756.
6. A. R. Lippert, V. L. Keleshian, J. W. Bode, Org. Biomol. Chem. 2009, 7, 1529-1532
7. K. M. Larson, M. He, J. F. Teichert, A. Naganawa, J.W. Bode, Chem. Sci. 2012, 3, 1825-1828.
8. A. G. Campaña, A. Carlone, K. Chen, D. T. F. Dryden, D. A. Leigh,U. Lewandowska, K. M. Mullen, Angew. Chem. 2012, 124, 5576-5579
9. Angew. Chem. Int. Ed. 2012, 51, 5480-5483.
10. S. Otto, Acc. Chem. Res. 2012, DOI: 10.1021/ar200246j.
11. J. B. Lambert, Tetrahedron Lett. 1963, 4, 1901-1906.
12. D. Cremer, P. Svensson, E. Kraka, P. Ahlberg, J. Am. Chem. Soc. 1993, 115, 7445-7456.
13. P. Ahlberg, D. L. Harris, S.Winstein, J. Am. Chem. Soc. 1970, 92, 4454-4456.
14. H. E. Zimmerman, G. L. Grunewald, J. Am. Chem. Soc. 1966, 88, 183-184
15. N. H. Werstiuk, Can. J. Chem. 2010, 88, 1195-1204.
16. W. von E. Doering, B. M. Ferrier, E. T. Fossel, J. H. Hartenstein, M. Jones, Jr., G. Klumpp, R. M. Rubin, M. Saunders, Tetrahedron 1967, 23, 3943-3963.
17. P. Ahlberg, J. B. Grutzner, D. L. Harris, S. Winstein, J. Am. Chem. Soc. 1970, 92, 3478-3480
18. T. S. Abram, W. E. Watts, J. Organomet. Chem. 1976, 105, C16-C18.
19. H. Tsuruta, K. Kurabayashi, T. Mukai, Bull. Chem. Soc. Jpn. 1972, 45, 2822-2828
20. C. Engdahl, G. Jonsäll, P. Ahlberg, J. Am. Chem. Soc. 1983, 105, 891-897
21. C. Engdahl, P. Ahlberg, J. Phys. Org. Chem. 1990, 3, 349-357.
22. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
23. E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346
24. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
25. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766-1775
26. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265
27. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
28. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221
29. M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448-2462.
30. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460
31. Angew. Chem. Int. Ed. 2004, 43, 2402-2406.
32. A. S. K. Hashmi, Angew. Chem. 2008, 120, 6856-6858
33. Angew. Chem. Int. Ed. 2008, 47, 6754-6756
34. P. Pérez-Galán, E. Herrero-Gómez, D. T. Hog, N. J. A. Martin, F. Maseras, A. M. Echavarren, Chem. Sci. 2011, 2, 141-149
35. P. Pérez-Galán, N. J. A. Martin, A. G. Campaña, D. J. Cárdenas, A. M. Echavarren, Chem. Asian J. 2011, 6, 482-486.
36. D. Benitez, N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard III, F. D. Toste, Nat. Chem. 2009, 1, 482-486
37. C. H. M. Amijs, V. López-Carrillo, M. Raducan, P. Pérez-Galán, C. Ferrer, A. M. Echavarren, J. Org. Chem. 2008, 73, 7721-7730.
38. L.-P. Liu,G. B. Hammond, Chem. Soc. Rev. 2012, 41, 3129-3139.
39. C. R. Solorio-Alvarado, Y. Wang, A. M. Echavarren, J. Am. Chem. Soc. 2011, 133, 11952-11955.
40. For ligand-controlled selectivity in gold-catalyzed transformations, see Ref. [13c, 16] and the following selected examples: D. Benitez, E. Tkatchouk, A. Z. Gonzalez, W. A. Goddard III, F. D. Toste, Org. Lett. 2009, 11, 4798-4801
41. C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127
42. Angew. Chem. Int. Ed. 2006, 45, 1105-1109.
43. P. K. Freeman, K. E. Swenson, J. Org. Chem. 1982, 47, 2040-2043.
44. S. López, E. Herrero-Gómez, P. Pérez-Galán, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 6175-6178
45. Angew. Chem. Int. Ed. 2006, 45, 6029-6032.
46. D. Bosse, A. de Meijere, Tetrahedron Lett. 1978, 19, 965-968.
47. J. Siegwarth, J. Bornhöft, C. Näther, R. Herges, Org. Lett. 2009, 11, 3450-3452.
48. Detailed procedures and characterization data are available in the Supporting Information. X-ray crystallography: CCDC 897922 (16/16'), 897923 (17), 897920 (18), and 897921 7v
49. see the Supporting Information) contain 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.
50. Although this cyclization could formally be seen as a direct 6-endo-dig process, calculations favor a cyclization involving the corresponding norcaradiene tautomer. See the Supporting Information for the reaction coordinate for the transformation of Id into IId (L=PMe3) and for additional computational details.
51. Similar minima were found for the phenylbarbaralyl gold species withAuCl,AuCl3,AuPMe3, andAuP(OMe3). In these structures, gold, rather than the phenyl substituent, stabilizes the carbocationic center.[25]