Gold-catalysis: Reactions of furandialkynes

Synthesis

Volumn , Issue 17, 2008, Pages 2707-2718

  Hashmi, A Stephen K ^a   Enns, Elisabeth ^a   Frost, Tanja M ^a   Schäfer, Sascha ^a   Frey, Wolfgang ^a   Rominger, Frank ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Benzofurans; Furans; Gold; Homogeneous catalysis; Spiro compounds

Indexed keywords

GOLD COMPOUNDS; PHENOLS;

ALKYNES; BENZOFURAN; BENZOFURANS; FURANS; GOLD-CATALYZED REACTIONS; HOMOGENEOUS CATALYSIS; HYDROXY GROUPS; SPIRO COMPOUNDS;

GOLD;

(5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 YLMETHYL)PROP 2 YNYLAMINE; (5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 YLMETHYLENE)PROP 2 YNYL AMINE; (5 ETHYNYLFURAN 2 YLMETHYL)PROP 2 YNYLAMINE; 4 METHYL N PROP 2 YNYL N (5 TRIMETHYLSILANYLETHYNYLFURAN 2 YLMETHYL)BENZENESULFONAMIDE; 5 (4 HYDROXYPENT 1 YNYL)FURAN 2 CARBALDEHYDE; 5 (5 HYDROXYPENT 1 YNYL)FURAN 2 CARBALDEHYDE; 5 (5 PROP 2 YNYLAMINOMETHYLFURAN 2 YL)PENT 4 YN 1 OL; 5 (5 PROP 2 YNYLAMINOMETHYLFURAN 2 YL)PENT 4 YN 2 OL; 5 (5 PROP 2 YNYLIMINOMETHYLFURAN 2 YL)PENT 4 YN 1 OL; 5 (5 PROP 2 YNYLIMINOMETHYLFURAN 2 YL)PENT 4 YN 2 OL; 5 [(4 METHOXYPHENYL)ETHYNYL] 2 FURALDEHYDE; 5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 CARBALDEHYDE; 5 TRIMETHYLSILANYLETHYNYLFURAN 2 CARBALDEHYDE; ALKYNE DERIVATIVE; BENZOFURAN DERIVATIVE; FURAN DERIVATIVE; GOLD CHLORIDE; N (5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 YLMETHYL) 4 METHYLBENZENESULFONAMIDE; N (5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 YLMETHYL) 4 N PROP 2 YNYLBENZENESULFONAMIDE; N (5 CYCLOHEX 1 ENYLETHYNYLFURAN 2 YLMETHYLENE) 4 METHYLBENZENESULFONAMIDE; N (5 ETHYNYLFURAN 2 YLMETHYL) 4 METHYL N PROP 2 YNYLBENZENESULFONAMIDE; N [5 (4 HYDROXYPENT 1 YNYL)FURAN 2 YLMETHYL]4 METHYL N PROP 2 YNYLBENZENESULFONAMIDE; N [5 (5 HYDROXYPENT 1 YNYL)FURAN 2 YLMETHYL] 4 METHYL N PROP 2 YNYL BENZESULFONAMIDE; N [[5 [(4 METHOXYPHENYL)ETHYNYL] 2 FURYL]METHYL] 4 METHYL N (PROP 2 YN 1 YL)BENZENESULFONAMIDE; N [[5 [(4 METHOXYPHENYL)ETHYNYL] 2 FURYL]METHYL]PROP 2 YN 1 AMINE; N [[5 [(4 METHOXYPHENYL)ETHYNYL] 2 FURYL]METHYLENE]PROP 2 YN 1 AMINE; PHENOL DERIVATIVE; PROP 2 YNYL (5 TRIMETHYLSILANYLETHYNYLFURAN 2 METHYLENE)AMINE; PROP 2 YNYL (5 TRIMETHYLSILANYLETHYNYNLFURAN 2 YLMETHYL)AMINE; TOLUENE 4 SULFONIC ACID 5 [5 [[PROP 2 YNYL(TOLUENE 4 SULFONYL)AMINO]METHYL]FURAN 2 YL]PENT 4 YNYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SONOGASHIRA REACTION;

EID: 51949106824     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067227     Document Type: Article

References (39)

1. (a) Dyker, G. Angew. Chem. Int. Ed. 2000, 39, 4237;
2. Angew. Chem. 2000, 112, 4407.
3. (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
4. (c) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
5. (d) Krause, N.; Hoffmann-Röder, A. Org. Biomol. Chem. 2005, 3, 387.
6. (e) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990;
7. Angew. Chem. 2005, 117, 7150.
8. (f) Hashmi, A. S. K.; Hutchings, G. Angew. Chem. Int. Ed. 2006, 45, 7896;
9. Angew. Chem. 2006, 118, 8064.
10. (g) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
11. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553.
12. Martín-Matute, B.; Cardenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2001, 40, 4754;
13. Angew. Chem. 2001, 113, 4890.
14. Méndez, M.; Munoz, M. P.; Nevade, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
15. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769.
16. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19.
17. Hashmi, A. S. K.; Kurpejovic, E.; Frey, W.; Bats, J. W. Tetrahedron 2007, 63, 5879.
18. Hashmi, A. S. K.; Wölfle, M.; Ata, F.; Hamzic, M.; Salathé, R.; Frey, W. Adv. Synth. Catal. 2006, 348, 2501.
19. Hashmi, A. S. K.; Wölfle, M.; Teles, J. H.; Frey, W. Synlett 2007, 1747.
20. Hashmi, A. S. K.; Ding, L.; Fischer, P.; Bats, J. W.; Frey, W. Chem. Eur. J. 2003, 9, 4339.
21. Hashmi, A. S. K.; Grundl, L. Tetrahedron 2005, 61, 6231.
22. Hashmi, A. S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem. Eur. J. 2008, 14, in press.
23. Hashmi, A. S. K.; Weyrauch, J. P.; Rudolph, M.; Kurpejovic, E. Angew. Chem. Int. Ed. 2004, 43, 6545;
24. Angew. Chem. 2004, 116, 6707.
25. Hashmi, A. S. K.; Blanco, M. C.; Kurpejovic, E.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2006, 348, 709.
26. Hashmi, A. S. K.; Haufe, P.; Schmid, C.; Rivas Nass, A.; Frey, W. Chem. Eur. J. 2006, 12, 5376.
27. Hashmi, A. S. K.; Salathé, R.; Frey, W. Chem. Eur. J. 2006, 12, 6991.
28. Hashmi, A. S. K.; Ata, F.; Kurpejovic, E.; Huck, J.; Rudolph, M. Top. Catal. 2007, 44, 245.
29. Hashmi, A. S. K.; Rudolph, M.; Siehl, H.-U.; Tanaka, M.; Bats, J. W.; Frey, W. Chem. Eur. J. 2008, 14, 3703.
30. Hashmi, A. S. K.; Rudolph, M.; Weyrauch, J. P.; Wölfle, M.; Frey, W.; Bats, J. W. Angew. Chem. Int. Ed. 2005, 44, 2798;
31. Angew. Chem. 2005, 117, 2858.
32. Hashmi, A. S. K.; Weyrauch, J. P.; Kurpejovic, E.; Frost, T. M.; Miehlich, B.; Frey, W.; Bats, J. W. Chem. Eur. J. 2006, 12, 5806.
33. Hashmi, A. S. K.; Kurpejovic, E.; Wölfle, M.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2007, 349, 1743.
34. (a) Monteiro, N.; Balme, G. Synlett 1998, 746.
35. (b) Yoshida, M.; Morishita, Y.; Fujita, M.; Ihara, M. Tetrahedron 2005, 61, 4381.
36. (c) Li, X.; Chianese, A. R.; Vogel, T.; Crabtree, R. H. Org. Lett. 2005, 7, 5437.
37. (d) Belting, V.; Krause, N. Org. Lett. 2006, 8, 4489.
38. CCDC 631589 (7c), 687063 (7g), 631588 (7h), 631590 (10e) and 687064 (15g) contain the supplementary crystallographic data for this paper. These data can be obtained online free of charge or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk
39. Gagosz, F. Org. Lett. 2005, 7, 4129.