Site-Selective Suzuki-Miyaura and Sonogashira Cross Coupling Reactions of the Bis(triflate) of 2,4'-Bis(hydroxy)diphenyl Sulfone

ChemCatChem

Volumn 4, Issue 3, 2012, Pages 356-362

  Khera, Rasheed Ahmad ^a,b   Ali, Asad ^a,c   Hussain, Munawar ^a   Ibad, Muhammad Farooq ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF AGRICULTURE   (Pakistan)

^c ABDUL WALI KHAN UNIVERSITY   (Pakistan)

Author keywords

Catalysis; Palladium; Site selectivity; Sonogashira reaction; Sulfones; Suzuki Miyaura reaction

Indexed keywords

CROSS COUPLING REACTIONS; SITE SELECTIVE; SITE-SELECTIVITY; SONOGASHIRA CROSS-COUPLING REACTION; SONOGASHIRA REACTION; SULFONES; SUZUKI-MIYAURA; SUZUKI-MIYAURA REACTION; TRIFLATES;

PALLADIUM;

CATALYSIS;

EID: 84857549419     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100257     Document Type: Article

References (92)

1. S. S. Shrimali, B. C. Joshi, D. Kishore, J. Indian Chem. Soc. 1988, 65, 438.
2. P. S. Upadhyay, R. N. Vansdadia, A. J. Baxi, Indian J. Chem. Sect. B 1990, 29, 793.
3. I. Teshirogi, S. Matsutani, K. Shirahase, Y. Fujii, T. Yoshida, J. Med. Chem. 1996, 39, 5183.
4. R. Paulini, C. Lerner, F. Diederich, R. Jakob-Roetne, G. Zuercher, E. Borroni, Helv. Chim. Acta 2006, 89, 1856.
5. P. G. deBenedetti, D. Iarossi, C. Menziani, V. Caiolfa, C. Frassineti, C. Cennamo, J. Med. Chem. 1987, 30, 459.
6. P. G. deBenedetti, D. Iarossi, U. Folli, C. Frassineti, M. C. Menziani, C. Cennamo, J. Med. Chem. 1989, 32, 2396.
7. I. Sircar, M. Hoefle, R. E. Maxwell, J. Med. Chem. 1983, 26, 1020.
8. L. D. Markley, Y. C. Tong, J. K. Dulworth, D. L. Steward, C. T. Goralski, J. Med. Chem. 1986, 29, 427.
9. J. Wright, G. Bolton, M. Creswell, D. Downing, L. Georgic, Bioorg. Med. Chem. Lett. 1996, 6, 1809.
10. N. Neamati, A. Mazumder, H. Zhao, S. Sunder, T. R. Burke, Jr., R. J. Schultz, Y. Pommier, Antimicrob. Agents Chemother. 1997, 41, 385.
11. J. H. Chan, J. S. Hong, R. N. Hunter, G. F. Orr, J. R. Cowan, D. B. Sherman, S. M. Sparks, B. E. Reitter, C. W. Andrews, Hazen, J. Richard, M. S. Clair, J. Med. Chem. 2001, 44, 1866.
12. J. R. Tagat, S. W. McCombie, R. W. Steensma, S.-I. Lin, D. V. Nazareno, B. Baroudy, N. Vantuno, S. Xu, J. Liu, Bioorg. Med. Chem. Lett. 2001, 11, 2143.
13. J. L. Stanton, E. Cahill, R. Dotson, J. Tan, H. C. Tomaselli, J. M. Wasvary, Z. F. Stephan, R. E. Steele, Bioorg. Med. Chem. Lett. 2000, 10, 1661.
14. J. A. Kozlowski, G. Zhou, J. R. Tagat, S.-I. Lin, S. W. McCombie, V. B. Ruperto, R. A. Duffy, R. A. McQuade, G. Crosby, L. A. Taylor, W. Billard, Bioorg. Med. Chem. Lett. 2002, 12, 791.
15. Y. Wang, S. Chackalamannil, Z. Hu, J. W. Clader, W. Greenlee, W. Billard, H. Binch, G. Crosby, V. Ruperto, R. A. Duffy, R. McQuade, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2000, 10, 2247.
16. C. D. Boyle, S. Chackalamannil, L.-Y. Chen, S. Dugar, P. Pushpavanam, W. Billard, H. Binch, G. Crosby, M. Cohen-Williams, V. L. Coffin, R. A. Duffy, Bioorg. Med. Chem. Lett. 2000, 10, 2727.
17. Y. Wang, S. Chackalamannil, W. Chang, W. Greenlee, V. Ruperto, R. A. Duffy, R. McQuade, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2001, 11, 891.
18. J. R. Tagat, S. W. McCombie, R. W. Steensma, S.-I. Lin, D. V. Nazareno, B. Baroudy, N. Vantuno, S. Xu, J. Liu, Bioorg. Med. Chem. Lett. 2001, 11, 2143.
19. C. D. Boyle, S. Chackalamannil, J. W. Clader, W. J. Greenlee, H. B. Josien, J. J. Kaminski, J. A. Kozlowski, S. W. McCombie, D. V. Nazareno, J. R. Tagat, Y. Wang, Bioorg. Med. Chem. Lett. 2001, 11, 2311.
20. C. D. Boyle, S. F. Vice, J. Campion, S. Chackalamannil, C. M. Lankin, S. W. McCombie, W. Billard, H. Binch, G. Crosby, M.-C. Williams, V. L. Coffin, Bioorg. Med. Chem. Lett. 2002, 12, 3479.
21. A. Sasse, X. Ligneau, B. Sadek, S. Elz, H. H. Pertz, C. R. Ganellin, J.-M. Arrang, J.-C. Schwartz, W. Schunack, H. Stark, Arch. Pharm. 2001, 334, 45.
22. R. F. Langler, R. L. Paddock, D. B. Thompson, I. Crandall, M. Ciach, K. C. Kain, Aust. J. Chem. 2003, 56, 1127.
23. B. J. Lavey, J. A. Kozlowski, R. W. Hipkin, W. Gonsiorek, D. J. Lundell, J. J. Piwinski, S. Narula, C. A. Lunn, Bioorg. Med. Chem. Lett. 2005, 15, 783.
24. I.-L. Lu, N. Mahindroo, P.-H. Liang, Y.-H. Peng, C.-J. Kuo, K.-C. Tsai, H.-P. Hsieh, Y.-S. Chao, S.-Y. Wu, J. Med. Chem. 2006, 49, 5154.
25. P. A. Magriotis, K. D. Kim, J. Am. Chem. Soc. 1993, 115, 2972.
26. J. A. Miller, G. Zweifel, J. Am. Chem. Soc. 1983, 105, 1383.
27. E. J. Corey, A. Tramontano, J. Am. Chem. Soc. 1984, 106, 462.
28. H. R. Marshall, M. Chobanian, M. Yanik, Org. Lett. 2001, 3, 4107.
29. M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc. 2004, 126, 14314.
30. M. Yoshida, Y. Ohsawa, M. Ihara, Tetrahedron Tetrahedron. 2006, 62, 11218.
31. J. K. Joseph, S. L. Jain, B. Sain, Synth. Commun. 2006, 36, 2743, and references therein.
32. D.-W. Chen, R. J. Kubiak, J. A. Ashley, K. D. Janda, J. Chem. Soc. Perkin Trans. 1 2001, 2796.
33. J. Marquie, A. Laporterie, J. Dubac, N. Roques, J.-R. Desmurs, J. Org. Chem. 2001, 66, 421.
34. S. Répichet, C. LeRoux, J. Dubac, Tetrahedron Lett. 1999, 40, 9233.
35. A. R. Hajipour, A. Zarei, L. Khazdooz, S. A. Pourmousavi, B. B. F. Mirjalili, A. E. Ruoho, Phosphorus Sulfur Silicon Relat. Elem. 2005, 180, 2029.
36. V. Woroshzow, V. Kutschkarow, Zh. Obshch. Khim. 1949, 19, 1943.
37. W. Zhu, D. Ma, J. Org. Chem. 2005, 70, 2696.
38. F. Huang, R. A. Batey, Tetrahedron 2007, 63, 7667.
39. B. P. Bandgar, S. V. Bettigeri, J. Phopase, Org. Lett. 2004, 6, 2105.
40. A. W. Erian, Y. Issac, S. M. Sherif, F. F. Mahmoud, J. Chem. Soc. Perkin Trans. 1 2000, 3686.
41. K. Ogura, M. Takeda, J. R. Xie, M. Akazome, S. Matsumoto, Tetrahedron Lett. 2001, 42, 1923.
42. S. Matsumoto, K. Kumazawa, K. Ogura, Bull. Chem. Soc. Jpn. 2003, 76, 2179.
43. L. Bianchi, C. Dell'Erba, M. Maccagno, A. Mugnoli, M. Novi, G. Petrillo, F. Sancassan, C. Tavani, J. Org. Chem. 2003, 68, 5254.
44. Y. Mutsuhiro, M. Watanabe, S. Furukawa, Chem. Pharm. Bull. 1990, 38, 902.
45. A. Padwa, Y. Gareau, B. Harrison, A. Rodriguez, J. Org. Chem. 1992, 57, 3540.
46. K. Hayakawa, H. Nishiyama, K. Kanematsu, J. Org. Chem. 1985, 50, 512.
47. J. Nakayama, A. Hirashima, J. Am. Chem. Soc. 1990, 112, 7648.
48. C.-M. Hu, F. Hong, B. Jiang, Y. Xu, J. Fluorine Chem. 1994, 66, 215.
49. B. Antelo, L. Castedo, J. Delamano, A. Gomes, C. Lopez, G. Tojo, J. Org. Chem. 1996, 61, 1188.
50. M. Shkoor, A. Riahi, O. Fatunsin, H. Reinke, C. Fischer, P. Langer, Synthesis 2009, 2223.
51. For reviews of cross coupling reactions of polyhalogenated heterocycles, see:.
52. S. Schröter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245.
53. M. Schnürch, R. Flasik, A. F. Khan, M. Spina, M. D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem. 2006, 3283.
54. For reactions of halogenated heterocycles from our group, see:.
55. T. T. Dang, T. T. Dang, R. Ahmad, H. Reinke, P. Langer, Tetrahedron Lett. 2008, 49, 1698.
56. T. T. Dang, A. Villinger, P. Langer, Adv. Synth. Catal. 2008, 350, 2109.
57. M. Hussain, T. H. Nguyen, P. Langer, Tetrahedron Lett. 2009, 50, 3929.
58. S.-M. TenghoToguem, M. Hussain, I. Malik, A. Villinger, P. Langer, Tetrahedron Lett. 2009, 50, 4962.
59. T. T. Dang, T. T. Dang, N. Rasool, A. Villinger, P. Langer, Adv. Synth. Catal. 2009, 351, 1595.
60. I. Ullah, R. A. Khera, M. Hussain, P. Langer, Tetrahedron Lett. 2009, 50, 4651.
61. For reactions of bis(triflates)from our group, see:.
62. M. Nawaz, M. FarooqIbad, A. Obaid-Ur-Rahman, R. A. Khera, A. Villinger, P. Langer, Synlett 2010, 150.
63. M. Nawaz, R. A. Khera, I. Malik, M. F. Ibad, O.-U. R. Abid, A. Villinger, P. Langer, Synlett 2010, 979.
64. O.-u.-R. Abid; M. F. Ibad, M. Nawaz, M. Sher, N. H. Rama, A. Villinger, P. Langer, Tetrahedron Lett. 2010, 51, 1541; M. F. Ibad, M. Nawaz, M. Sher, N. H. Rama, A. Villinger, P. Langer, Tetrahedron Lett. 2010, 51, 1541; A. Mahal, A. Villinger, P. Langer, Synlett 2010, 1085.
65. A. Ali, R. A. Khera, M. F. Ibad, M. Hussain, A. Villinger, P. Langer, Synlett 2010, 731; R. Hara, Y. Liu, W.-H. Sun, T. Takahashi, Tetrahedron Lett. 1997, 38, 4103.
66. For reviews of the Suzuki reaction, see:.
67. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
68. A. Suzuki in Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, 2002, chap. III. 2.2.
69. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516; Angew. Chem. Int. Ed. 2005, 44, 4442.
70. CCDC848539 and CCDC848540 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
71. V. Cadierno, M. P. Gamasa, J. Gimeno, J. Organomet. Chem. 2001, 39, 621.
72. M. Koreeda, W. Yang, Synlett 1994, 201.
73. M. Z. Cai, D. Wang, P. Wang, J. Chem. Res. 2006, 504.
74. J. W. Jiang, M. Z. Cai, Chin. Chem. Lett. 2006, 17, 757.
75. A. L. Braga, G. Zeni, L. H. Andrade, C. C. Silveira, H. A. Stefani, Synthesis 1998, 39.
76. Y. Ma, X. Huang, Synth. Commun. 1997, 27, 3441.
77. M. Z. Cai, C. Y. Peng, H. Zhao, J. Chem. Res. 2002, 376.
78. P. Zhong, N. Huang, Synth. Commun. 2002, 32, 139.
79. X. Huang, Y. P. Wang, Tetrahedron Lett. 1996, 37, 7417.
80. M. Cai, J. Z. Chen, J. Chem. Res. 2004, 840.
81. N. Chatani, N. Amishiro, S. Murai, J. Am. Chem. Soc. 1991, 113, 7778.
82. M. Z. Cai, W. Hao, H. Zhao, C. Song, J. Chem. Res. 2003, 485.
83. X. Huang, P. Zhong, J. Chem. Soc. Perkin Trans. 1 1999, 1, 1543.
84. M. Z. Cai, H. Zhao, H. Ye, J. Xia, C. Song, J. Chem. Res. 2003, 344.
85. M. Yoshida, S. Yoshikawa, T. Fukuhara, N. Yoneda, S. Hara, Tetrahedron 2001, 57, 7143.
86. J. Legros, B. Crousse, J. P. Begue, J. Fluorine Chem. 2001, 107, 121.
87. M. Yoshimatsu, J. Hasegawa, J. Chem. Soc. Perkin Trans. 1 1997, 211.
88. Y. Shen, G. Wang, J. Sun, J. Chem. Soc. Perkin Trans. 1 2001, 519.
89. For reviews of Sonogashira reactions, see:.
90. K. Sonogashira in Metal-Catalyzed Cross-Coupling Reactions, Wiley VCH, 1998, p.203.
91. K. Sonogashira in Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, 2002, chap. III 2-8, p.493.
92. J. P. Genet, E. Blart, M. Savignac, Synlett 1992, 715.