Gold catalysis: Tandem reactions of diyne-diols and external nucleophiles as an easy access to tricyclic cage-like structures

Chemistry - A European Journal

Volumn 16, Issue 32, 2010, Pages 9846-9854

  Hashmi, A Stephen K ^a   Bührle, Miriam ^a   Wölfle, Michael ^b   Rudolph, Matthias ^a   Wieteck, Marcel ^a   Rominger, Frank ^a   Frey, Wolfgang ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Alcohols; Alkynes; Amines; Gold; Heterocycles

Indexed keywords

ALKYNES; BI-DIRECTIONAL SYNTHESIS; CAGE COMPOUNDS; CAGE-LIKE STRUCTURES; CARBENES; CROSS-COUPLINGS; CRYSTAL STRUCTURE ANALYSIS; DIASTEREOMERS; GOLD CATALYSIS; GOLD CATALYSTS; HETEROCYCLES; HOMOPROPARGYLIC ALCOHOLS; HYDROAMINATIONS; INTERNAL ALKYNES; LINKING GROUPS; MULTI-STEP; PALLADIUM CATALYSIS; REACTION PATHWAYS; TANDEM REACTION;

ACETYLENE; AMINES; CATALYSIS; GOLD; NUCLEOPHILES; ORGANIC POLYMERS; PALLADIUM; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CRYSTAL STRUCTURE;

EID: 77955865116     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001322     Document Type: Article

References (54)

1. a) A. S. K. Hashmi, G. X Hutchings, Angew. Chem. 2006, 118, 8064-8105;
2. Angew. Chem. Int. Ed, 2006, 45, 7896-7936;
3. b) A. Fürstner, P.W. Davis, Angew. Chem. 2007, 119, 3478-3519;
4. Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
5. c) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
6. d) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
7. e) A. Arcadi, Chem. Rev. 2008, 108, 3266-3325;
8. f) E. Jiménez-Nunez, A.M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
9. g) Z. G. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265.
10. Y. Fukuda, K. Utimoto, J. Org. Chem, 1991, 56, 3729-3731.
11. For some representative examples for hydrations and hydroalkoxylations of alkynes, see: a) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478;
12. Angew. Chem. Int. Ed. 1998, 37, 1415-1418;
13. b) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T.M. Frost, Angew. Chem. 2000, 112, 2382-2385;
14. Angew. Chem. Int. Ed. 2000, 39, 2285-2288;
15. c) A. Arcadi, G. Cerichelli, M. Chiarini, S. Di Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198;
16. d) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 2002, 114, 4745-4747;
17. Angew. Chem. Int. Ed. 2002, 41, 4563-4565;
18. e) P. Roembke, H. Schmidbaur, S. Cronje, H. Raubenheimer, J. Mol. Cat. A 2004, 212, 35-42;
19. f) L. L. Santos, V.R. Ruiz, M. J. Sabater, A. Corma, Tetrahedron 2008, 64, 7902-7909;
20. g) N. Marion, R. S. Ramón, S. P. Nolan, J. Am. Chem. Soc. 2008, 130, 448-449;
21. h) A. Leyva, A. Corma, J. Org. Chem. 2009, 74, 2067-2074;
22. A. S. K. Hashmi, S. Schäfer, M. Wölfle, C. Diez Gil, P. Fischer, A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. 2007, 119, 6297-6300;
23. Angew. Chem. Int. Ed. 2007, 46, 6184-6187.
24. a) S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt, J. Am. Chem. Soc. 2005, 127, 9976-9977;
25. b) B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907-4910;
26. c) L.-Z. Dai, M.-J. Qi, Y.-L. Shi, X.-G. Liu, M. Shi, Org. Lett 2007, 9, 3191-3194;
27. d) Y. Li, F. Zhou, C. J. Forsyth, Angew. Chem. 2007, 119, 283-286;
28. Angew. Chem. Int. Ed. 2007, 46, 279-282;
29. e) Y. Zhang, J. Xue, Z. Xin, Z. Xie, Y. Li, Synlett 2008, 940-944;
30. f) L.-P. Liu, G. B. Hammond, Org. Lett. 2009, 11, 5090-5092;
31. g) A. Diéguez-Vázquez, C. C. Tzschucke, J. Crecente-Campo, S. McGrath, S. V. Ley, Eur. J. Org. Chem. 2009, 1698-1706.
32. For mechanistically related reactions, see also: a) L.-Z. Dai, M. Shi, Chem. Eur. J. 2008, 14, 7011-7018;
33. b) A. Aponick, C.-Y. Li, J. A. Palmes, Org. Lett. 2009, 11, 121-124;
34. c) J. Meng, Y.L. Zhao, C.-Q. Ren, Y. Li, Z. Li, Q. Liu, Chem. Eur. J. 2009, 15, 1830-1834.
35. J. Barluenga, A. Diéguez, A. Fernández, F. Rodríguez, F. J. Fananás, Angew. Chem, 2006, 118, 2145-2147;
36. Angew. Chem. Int. Ed. 2006, 45, 2091-2093.
37. CCDC-777469 (syn-2b), 777470 (syn-2e), 777471 (2g), 777472 (3a), 777473 (3b), 777474 (3c), 777475 (3d), 777476 (4), 777477 (5a), 777478 (5b), 777479 (5c), 777480 (5f), 777481 (5g), 777482 (5i), 777483 (51), 777484 (5p), 777485 (5r), 777486 (6), 777487 (8) and 777488 (9) 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.
38. M. Bolte, K. Eckstein, A. S. K. Hashmi, Acta Crystallogr. Sect. E 2005, 61, o4064-o4066.
39. a) J. Vicente, M. Chicote, M. Abrisqueta, P. G. Jones, Organometallics 1997, 16, 5628-5636;
40. b) C. Bartolomé, Z. Ramiro, D. GarcíaCuadrado, P. Pérez-Galán, M. Raducan, C. Bour, A. M. Echavarren, P. Espinet, Organometallics 2010, 29, 951-956;
41. c) A. S. K. Hashmi, T. Hengst, C. Lothschütz, F. Rominger, Adv. Synth. Catal. 2010, 352, 1315-1337.
42. a) A silver-catalysed acetalisation was reported in: C.H. Oh, H. J. Yi, J. H. Lee, New J. Chem. 2007, 31, 835-837;
43. b) for a comparison of the catalytic activity of silver and gold, see: A. S. K. Hashmi in Silver in Organic Chemistry (Ed. M. Harmanta), Wiley, Hoboken. 2010, pp. 357-379.
44. A. S. K. Hashmi, A. Loos, A. Littmann, I. Braun, J. Knight, S. Doherty, F. Rominger, Adv. Synth. Catal. 2009, 351, 576-582.
45. For representative examples of the gold-catalysed phenol synthesis, see: a) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554;
46. b) A.S.K. Hashmi, M. Rudolph, H.-U. Siehl, M. Tanaka, J. W. Bats, W. Frey, Chem. Eur. J. 2008, 14, 3703-3708;
47. for diols in the phenol synthesis, see: c) A. S. K. Hashmi, M. Wölfle, J. H. Teles, W. Frey, Synlett 2007, 1747-1752.
48. A. S. K. Hashmi, Angew. Chem. 2010, 122, DOI: 10.1002/ ange.200907078;
49. Angew. Chem. Int. Ed. 2010, 49, DOI: 10.1002/ anie. 200907078.
50. For a two-fold gold-catalysed addition to alkynes (hydroarylation), see: A. S. K. Hashmi, M. C. Blanco, Eur. J. Org. Chem. 2006, 4340-4342.
51. For the potential role/competition of protons in gold catalysis, see: a) A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blanco, Adv. Synth. Catal. 2006, 348, 705-708;
52. b) A. S. K. Hashmi, Catal. Today 2007, 122, 211-214.
53. For a report on a similar switch to the formation of a six-membered ring by a substituent on an alkyne in gold catalysis, see: A. S. K. Hashmi, A. Schuster, F. Rominger, Angew. Chem. 2009, 121, 83968398;
54. Angew. Chem. Int. Ed. 2009, 48, 8247-8249.