Microwave-assisted Ullmann-Buchwald C-S bond formation using a copper(I) catalyst and trans-cyclohexane-1,2-diol as ligand

Arkivoc

Volumn 2012, Issue 7, 2012, Pages 294-313

  Bagley, Mark C ^a   Fusillo, Vincenzo ^b   Hills, Edward G B ^a   Mulholland, Alex T ^a   Newcombe, Joseph ^a   Pentecost, Leanne J ^a   Radley, Emily L ^a   Stephens, Bethan R ^b   Turrell, Christopher C ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Copper; Microwaves; Sulfides; Ullmann condensation

Indexed keywords

EID: 84869741991     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0013.720     Document Type: Article

References (64)

1. (a) Tiecco, M. Synthesis 1988, 749.
2. (b) Lindley, J. Tetrahedron 1984, 40, 1433.
3. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
4. (b) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853.
5. (c) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
6. Thomas, A. W.; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 5400.
7. (a) Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J. Comb. Chem. 2010, 12, 422.
8. (b) Sreedhar, B.; Reddy, P. S.; Reddy, M. A. Synthesis 2009, 1732.
9. (c) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith III, W. J. J. Org. Chem. 1998, 63, 6338.
10. (d) Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654.
11. (e) Yuan, Y.; Thomé, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892.
12. (a) Kondo, T.; Mitsudo, T.-a. Chem. Rev. 2000, 100, 3205.
13. (b) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
14. (c) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
15. (d) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
16. (e) Velmathi, S.; Vijayaraghavan, R.; Amarendar, Ch.; Pal, R. P.; Vinu, A. Synlett 2010, 2733.
17. (f) Jammi, S.; Barua, P.; Rout, L.; Saha, P.; Punniyamurthy, T. Tetrahedron Lett. 2008, 49, 1484.
18. (g) Wu, W.-Y.; Wang, J.-C.; Tsai, F.-Y. Green Chem. 2009, 11, 326.
19. (h) Gonzalez-Arellano, C.; Luque, R.; Macquarrie, D. J. Chem. Commun. 2009, 1410.
20. (i) Gendre, F.; Yang, M.; Diaz, P. Org. Lett. 2005, 7, 2719.
21. (j) Park, N.; Park, K.; Jang, M.; Lee, S. J. Org. Chem. 2011, 76, 4371.
22. (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
23. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
24. (c) Hickman, R. J. S.; Christie, B. J.; Guy, R. W.; White, T. J. Aust. J. Chem. 1985, 38, 899.
25. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
26. (e) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
27. (f) Varala, R.; Ramu, E.; Mujahid Alam M.; Adapa, S. R. Chem. Lett. 2004, 33, 1614.
28. (g) Carril, M.; SanMartin, R.; Dominguez, E.; Tellitu, I. Chem. Eur. J. 2007, 13, 5100.
29. (h) Lindley, J. Tetrahedron, 1984, 40, 1433.
30. (i) Herrero, M. T.; SanMartin, R.; Domínguez, E. Tetrahedron 2009, 65, 1500.
31. (a) Buranaprasertsuk, P.; Chang, J. W. W.; Chavasiri, W.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 2023.
32. (b) Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 640.
33. (c) Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625.
34. (d) Prasad, D. J. C.; Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2009, 50, 1411.
35. (e) Xu, H.-J.; Liang, Y.-F.; Zhou, X.-F.; Feng, Y.-S. Org. Biomol. Chem. 2012, 10, 2562.
36. Wu, Y.-J.; He, H. Synlett 2003, 1789.
37. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
38. (a) Caddick, S.; Fitzmaurice, R. Tetrahedron 2009, 65, 3325.
39. (b) Kappe, C. O. Chem. Soc. Rev. 2008, 37, 1127.
40. (c) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
41. Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141.
42. (a) Nilsson, P.; Olofsson, K.; Larhed, M. Top. Curr. Chem. 2006, 266, 103.
43. (b) Singh, B. K.; Kaval, N.; Tomar, S.; Van der Eycken, E.; Parmar, V. S. Org. Process Res. Dev. 2008, 12, 468.
44. (a) Kappe, C. O.; Stadler, A. in Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
45. (b) Kappe, C. O.; Dallinger, D. Nat. Rev. Drug Discovery 2006, 5
46. (c) Spencer, J. Future Med. Chem. 2010, 2, 161.
47. (d) Wannberg, J.; Ersmark, K.; Larhed, M. Top. Curr. Chem. 2006, 266, 167.
48. (e) Alcázar, J.; Oehlrich, D. Future Med. Chem. 2010, 2, 169.
49. (a) Bagley, M. C.; Davis, T.; Dix, M. C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D. J. Org. Chem. 2009, 74, 8336.
50. (b) Bagley, M. C.; Davis, T.; Dix, M. C.; Rokicki, M. J.; Kipling, D. Bioorg. Med. Chem. Lett. 2007, 17, 5107.
51. Bagley, M. C.; Davis, T.; Murziani, P. G. S.; Widdowson, C. S.; Kipling, D. Pharmaceuticals 2010, 3, 1842.
52. Bagley, M. C.; Dix, M. C.; Fusillo, V. Tetrahedron Lett. 2009, 50, 3661.
53. Bagley, M. C.; Davis, T.; Dix, M. C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D. Future Med. Chem. 2010, 2, 1417.
54. (a) Bagley, M. C.; Lin, Z.; Pope, S. J. A. Dalton Trans. 2010, 39, 3163.
55. (b) Bagley, M. C.; Lin, Z.; Phillips, D. J.; Graham, A. G. Tetrahedron Lett. 2009, 50, 6823.
56. (a) Hoogenboom, R.; Wilms, T. F. A.; Erdmenger, T.; Schubert, U. S. Aust. J. Chem. 2009, 62, 236.
57. (b) Razzaq, T.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 6321.
58. (c) Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 4651.
59. Kornblum, N. J. Org. Chem. 1976, 41, 1560.
60. Pierini, A. B.; Baumgartner, M. T.; Rossi, R. A. J. Org. Chem. 1991, 56, 580.
61. Rastelli, G.; Ferrari, A. M.; Costantino, L.; Gamberini, M. C. Bioorg. Med. Chem. 2002, 10, 1437.
62. Takeuchi, H.; Hiyama, T.; Kamai, N.; Cya, H. J. Chem. Soc., Perkin Trans. 2 1997, 2301.
63. Bass, S. L.; Johnson, T. B. J. Am. Chem. Soc. 1930, 52, 1146.
64. Pathak, A. K.; Pathak, V.; Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2004, 47, 273.