Synthesis of substituted thiophenes by palladium-catalyzed heterocyclodehydration of 1-mercapto-3-yn-2-ols in conventional and nonconventional solvents

Journal of Organic Chemistry

Volumn 77, Issue 21, 2012, Pages 9905-9909

  Gabriele, Bartolo ^a   Mancuso, Raffaella ^a   Veltri, Lucia ^a   Maltese, Vito ^a   Salerno, Giuseppe ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; HIGH YIELD; MOLAR RATIO; PALLADIUM-CATALYZED; SUBSTITUTED THIOPHENE;

IONIC LIQUIDS; POTASSIUM IODIDE; THIOPHENE;

SOLVENTS;

1 MERCAPTO 2,2 DIALKYNYL 2 OLS; ALKYNYL GROUP; IONIC LIQUID; PALLADIUM; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HETEROCYCLODEHYDRATION; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; IONIC LIQUIDS; MOLECULAR STRUCTURE; PALLADIUM; SOLVENTS; THIOPHENES;

EID: 84868348787     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301943k     Document Type: Article

References (44)

1. Tsuchikama, K.; Hashimoto, Y.; Endo, K.; Shibata, T. Adv. Synth. Catal. 2009, 351, 2850-2854
2. Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002-5005
3. Aponick, A.; Li, C.-Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624-4627
4. Yada, Y.; Miyake, Y.; Nishibayashi, Y. Organometallics 2008, 27, 3614-3617
5. Hayes, S. J.; Knight, D. W.; Menzies, M. D.; O'Halloran, M.; Tan, W.-F. Tetrahedron Lett. 2007, 48, 7709-7712
6. Knight, D. W.; Sharland, C. M. Synlett 2004, 119-121
7. Sakai, M.; Sasaki, M.; Tanino, K.; Miyashita, M. Tetrahedron Lett. 2002, 43, 1705-1708
8. McDonald, F. E.; Zhu, H. Y. H. Tetrahedron 1997, 53, 11061-11068
9. McDonald, F. E.; Gleason, M. M. J. Am. Chem. Soc. 1996, 118, 6648-6659
10. McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D. J. Org. Chem. 1993, 58, 6952-6953
11. Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655-3661
12. Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277-4278
13. Gabriele, B.; Mancuso, R.; Maltese, V.; Veltri, L.; Salerno, G. J. Org. Chem. 2012, 77, 8657-8668
14. Gabriele, B.; Veltri, L.; Mancuso, R.; Salerno, G.; Maggi, S.; Aresta, B. M. J. Org. Chem. 2012, 77, 4005-4016
15. Gabriele, G.; Mancuso, R.; Lupinacci, E.; Veltri, L.; Salerno, G.; Carfagna, C. J. Org. Chem. 2011, 76, 8277-8286
16. Gabriele, B.; Plastina, P.; Vetere, M. V.; Veltri, L.; Mancuso, R.; Salerno, G. Tetrahedron Lett. 2010, 51, 3565-3567
17. Gabriele, B.; Veltri, L.; Mancuso, R.; Plastina, P.; Salerno, G.; Costa, M. Tetrahedron Lett. 2010, 51, 1663-1665
18. Gabriele, B.; Mancuso, R.; Lupinacci, E.; Spina, R.; Salerno, G.; Veltri, L.; Dibenedetto, A. Tetrahedron 2009, 65, 8507-8512
19. Gabriele, B.; Mancuso, R.; Salerno, G.; Lupinacci, E.; Ruffolo, G.; Costa, M. J. Org. Chem. 2008, 73, 4971-4977
20. Gabriele, B.; Mancuso, R.; Salerno, G.; Ruffolo, G.; Plastina, P. J. Org. Chem. 2007, 72, 6873-6877
21. Liu, Y.; Liu, Y.; Zhan, X. Macromol. Chem. Phys. 2011, 212, 428-443
22. Ivonin, S. P.; Tolmachev, A. A.; Pinchuk, A. M. Curr. Org. Chem. 2008, 12, 25-38
23. Sperry, J. B.; Wright, D. L. Curr. Opin. Drug Discovery Dev. 2005, 8, 723-740
24. Barbarella, G.; Melucci, M.; Sotgiu, G. Adv. Mater. 2005, 17, 1581-1593
25. Guernion, N. J. L.; Hayes, W. Curr. Org. Chem. 2004, 8, 637-651
26. Angelici, R. J. Organometallics 2001, 20, 1259-1275
27. Roncali, J. Chem. Rev. 1992, 92, 711-738
28. Mishra, P.; Maurya, H. K.; Tandon, V. K.; Kumar, B.; Ram, V. J. Tetrahedron Lett. 2012, 53, 1056-1059
29. Teiber, M.; Mueller, T. J. J. Chem. Commun. 2012, 48, 2080-2082
30. Robertson, F. J.; Wu, J. J. Am. Chem. Soc. 2012, 134, 2775-2780
31. Sammes, P. G.; Weller, D. J. Synthesis 1995, 1205-1222
32. Jung, M. J.; Piizzi, G. Chem. Rev. 2005, 105, 1735-1766
33. Patel, D. D. Chem. Rec. 2012, 12, 329-355
34. Wong, W.-L.; Wong, K.-Y. Can. J. Chem. 2012, 90, 1-16
35. Payagala, T.; Armstrong, D. W. Chirality 2012, 24, 17-53
36. Dupont, J. Acc. Chem. Res. 2011, 44, 1223-1231
37. Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508-3576
38. Hubbard, C. D.; Illner, P.; van Eldik, R. Chem. Soc. Rev. 2011, 40, 272-290
39. Zhang, Q.; Zhang, S.; Deng, Y. Green Chem. 2011, 13, 2619-2637
40. Gabriele, B.; Mancuso, R.; Salerno, G.; Larock, R. C. J. Org. Chem. 2012, 77, 7640-7645
41. Eichinger, K.; Mayr, P.; Nussbaumer, P. Synthesis 1989, 210-211
42. Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351-352
43. Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 156-164
44. Crosthwaite, J. M.; Aki, S. N. V. K.; Maginn, E. J.; Brennecke, J. F. J. Phys. Chem. B 2004, 108, 5113-5119