Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

Chemistry - A European Journal

Volumn 18, Issue 34, 2012, Pages 10480-10486

  Hashmi, A Stephen K ^a,b   Häffner, Tobias ^a   Yang, Weibo ^a   Pankajakshan, Sreekumar ^b   Schäfer, Sascha ^b   Schultes, Lara ^a   Rominger, Frank ^a   Frey, Wolfgang ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

alkynes; carbocations; furans; gold; heterocycles; reaction mechanisms

Indexed keywords

ALKYNES; CARBOCATIONS; FURANS; HETEROCYCLES; REACTION MECHANISM;

AROMATIC COMPOUNDS; GOLD; ORGANIC POLLUTANTS;

ACETYLENE;

EID: 84865042946     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200306     Document Type: Article

References (36)

1. A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; for recent results on furan synthesis, see
2. J. Chen, S. Ma, Chem. Asian J. 2010, 5, 2415-2421
3. X. Zhang, Z. Lu, C. Fu, S. Ma, J. Org. Chem. 2010, 75, 2589-2598; for a review, see
4. A. S. K. Hashmi, Pure Appl. Chem. 2010, 82, 1517-1528.
5. Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406.
6. Y. Fukuda, K. Utimoto, J. Org. Chem. 1991, 56, 3729-3731
7. J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478
8. Angew. Chem. Int. Ed. 1998, 37, 1415-1418
9. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385
10. Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
11. See compounds 36 e, 39 d, and 39 e in, A. S. K. Hashmi, P. Haufe, C. Schmid, A. Rivas Nass, W. Frey, Chem. Eur. J. 2006, 12, 5376-5382 (for compounds).
12. A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. Hamzic, Angew. Chem. 2009, 121, 5962-5966
13. Angew. Chem. Int. Ed. 2009, 48, 5848-5852.
14. A. S. K. Hashmi, S. Pankajakshan, M. Rudolph, E. Enns, T. Bander, F. Rominger, W. Frey, Adv. Synth. Catal. 2009, 351, 2855-2875.
15. A. S. K. Hashmi, W. Yang, F. Rominger, Angew. Chem. 2011, 123, 5882-5885
16. Angew. Chem. Int. Ed. 2011, 50, 5762-5765.
17. A. S. K. Hashmi, Angew. Chem. 2008, 120, 6856-6858
18. Angew. Chem. Int. Ed. 2008, 47, 6754-6756
19. for the formulation as the corresponding cyclopropyl carbenoid, see:, A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360-5369
20. Angew. Chem. Int. Ed. 2010, 49, 5232-5241.
21. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805
22. S. F. Kirsch, J. T. Binder, C. Liebert, H. Menz, Angew. Chem. 2006, 118, 6010-6013
23. Angew. Chem. Int. Ed. 2006, 45, 5878-5880
24. J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859
25. Angew. Chem. Int. Ed. 2006, 45, 6704-6707
26. C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127
27. Angew. Chem. Int. Ed. 2006, 45, 1105-1109
28. S. Labsch, S. Ye, A. Adler, J.-M. Neuörfl, H.-G. Schmalz, Tetrahedron: Asymmetry 2010, 21, 1745-1751; for related spiro intermediates, see
29. G. Cera, P. Crispino, M. Monari, M. Bandini, Chem. Commun. 2011, 47, 7803-7805
30. A. S. K. Hashmi, W. Yang, F. Rominger, Adv. Synth. Catal. 2012, 354, 1273-1279
31. A. S. K. Hashmi, W. Yang, F. Rominger, Chem. Eur. J. 2012, 18, 6576-6580.
32. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136.
33. CCDC-841976 (3 a), CCDC-839078 (2 f), CCDC-839079 (3 k), CCDC-839080 (2 t), and CCDC-839081 (4 x) 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.
34. A. S. K. Hashmi, A. Loos, S. Doherty, J. G. Knight, K. J. Robson, F. Rominger, Adv. Synth. Catal. 2011, 353, 749-759; for early results, see
35. A. S. K. Hashmi, M. Wölfle, F. Ata, M. Hamzic, R. Salathé, W. Frey, Adv. Synth. Catal. 2006, 348, 2501-2508.
36. A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771, compound 13 there.