Directed ortho -metalation-cross-coupling strategies. One-pot Suzuki reaction to biaryl and heterobiaryl sulfonamides

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3588-3591

  Schneider, Cédric ^a   Broda, Ellen ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; METAL; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; METALS; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONAMIDES;

EID: 79960151755     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201175g     Document Type: Article

References (68)

1. Watanabe, H.; Gay, R. L.; Hauser, C. R. J. Org. Chem. 1968, 33, 900
2. Watanabe, H.; Schwarz, R. A.; Hauser, C. R.; Lewis, J.; Slocum, D. W. Can. J. Chem. 1969, 47, 1543
3. Snieckus, V. Chem. Rev. 1990, 90, 879
4. Hartung, C. G. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: New York, 2002; p 330.
5. Macklin, T.; Snieckus, V. In Handbook of C-H Transformations: Dyker, G., Ed.; Wiley-VCH: New York, 2005; p 106.
6. Macor, J. E., Ed. Annual Reports in Medicinal Chemistry; Elsevier Acadmic Press: 2008, San Diego; Vol. 43, pp 14, 32, 35, 151, 164, 196.
7. Hansch, C.; Sammes, P. G.; Taylor, J. B. Comprehensive Medicinal Chemistry, Vol. 2; Pergamon Press: Oxford, 1990; Chapter 7.1.
8. Antibacterial: Bhusari, K. P.; Khedekar, P. B.; Umathe, S. N.; Behekar, R. H.; Rao, A. R. R. Indian J. Heterocycl. Chem. 2000, 9, 213
9. Antiviral: Eckenberg, P.; Reefschläger, J.; Bender, W.; Goldmann, S.; Harter, M.; Hallenberger, S.; Keldenich, J.; Weber, O.; Henninger, K. DE19934272, 2001; Chem. Abstr. 2001, 134, 115865.
10. Anticonvulsant and anti-inflammatory agents: Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 3 rd ed.; Thieme: Stuttgart, 1999.
11. Antihypertensive: Kanda, Y.; Kawanishi, Y.; Oda, K.; Sakata, T.; Mihara, S.; Asakura, K.; Kanemasa, T.; Ninomiya, M.; Fujimoto, M.; Kanoike, T. Bioorg. Med. Chem. 2001, 9, 897
12. Antiglaucoma: Mincione, F.; Starnotti, M.; Menabuoni, L.; Scozzafava, A.; Casini, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2001, 11, 1787
13. Antifungal: Ezabadi, I. R.; Camoutsis, C.; Zoumpoutlakis, P.; Geronikaki, A.; Soković, M.; Glamočilija, J.; Čirič, A. Bioorg. Med. Chem. 2008, 16, 1150
14. Sildenafil Citrate (Viagra): Noss, M. B.; Christ, G. J.; Melman, A. Drugs Today 1999, 35, 211
15. Brock, G. Drugs Today 2000, 36, 125
16. Amprenavir (Agenerase): Adkins, J.; Fauds, D. Drugs 1998, 55, 837
17. Conway, B.; Shafran, S. D. Expert. Opin. Invest. Drugs 2000, 9, 371
18. Reviews: Wilden, J. D. J. Chem. Res. 2010, 34, 510
19. Familoni, O. B. Synlett 2002, 8, 1181
20. Blanchet, J.; Macklin, T.; Ang, P.; Metallinos, C.; Snieckus, V. J. Org. Chem. 2007, 72, 3199
21. MacNeil, S. L.; Familoni, O. B.; Snieckus, V. J. Org. Chem. 2001, 66, 3662
22. Metallinos, C.; Nerdinger, S.; Snieckus, V. Org. Lett. 1999, 1, 1183
23. MacNeil, S. L. Ph.D. Thesis, 2001, Queen's University, Canada.
24. Alessi, M.; Larkin, A. L.; Olgivie, K. A.; Green, L. A.; Lai, S.; Lopez, S.; Snieckus, V. J. Org. Chem. 2007, 72, 1588
25. Sulfonamides are generally recalcitrant groups: Shohji, N.; Kawaji, T.; Okamoto, S. Org. Lett. 2011, 13, 2626 For their Corriu-Kumada cross-coupling excision
26. Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 888
27. Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 892
28. For secondary sulfonamides: Wu, X.; Wan, Y.; Mahalingam, A. K.; Murugaiah, A. M. S.; Plouffe, B.; Botros, M.; Karlén, A.; Hallberg, M.; Gallo-Payet, N.; Alterman, M. J. Med. Chem. 2006, 49, 7160
29. Jia, Z. J.; Wu, Y.; Huang, W.; Goldman, E.; Zhang, P.; Woolfrey, J.; Wong, P.; Huang, B.; Sinha, U.; Park, G.; Reed, A.; Scarborough, R. M.; Zhu, B.-Y. Bioorg. Med. Chem. Lett. 2002, 12, 1651
30. Su, T.; Wu, Y.; Doughan, B.; Jia, Z. J.; Woolfrey, J.; Huang, B.; Wong, P.; Park, G.; Sinha, U.; Scarborough, R. M.; Zhu, B.-Y. Bioorg. Med. Chem. Lett. 2001, 11, 2947
31. Quan, M. L.; Liauw, A. Y.; Ellis, C. D.; Pruitt, J. R.; Carini, D. J.; Bostrom, L. L.; Huang, P. P.; Harrison, K.; Knabb, R. M.; Thoolen, M. J.; Wong, P. C.; Wexler, R. R. J. Med. Chem. 1999, 42, 2752
32. For tertiary sulfonamides: Polniaszek, R. P.; Wang, X.; Thottathil, J.; Denzel, T. Appl. Int. WO 2002/032884, 2002
33. Chem. Abstr. 2002, 136, 325535.
34. For other methods, see: Ipso -borodesilylation: Zhao, Z.; Snieckus, V. Org. Lett. 2005, 7, 2523
35. 2 borylation: Cheung, W. S.; Parks, D. J.; Parsons, W. H.; Patel, S.; Player, M. R. Appl. Int. WO 2008/076752, 2008
36. Chem. Abstr. 2007, 149, 79605.
37. Hall, D. G., Ed. Boronic Acids; Wiley-VCH: Weinheim, 2005, p 14.
38. For previous syntheses, see: Lin, Q.; Meloni, D.; Pan, Y.; Xia, M.; Rodgers, J.; Shepard, S.; Li, M.; Galya, L.; Metcalf, B.; Yue, T.-Y.; Liu, P.; Zhou, J. Org. Lett. 2009, 11, 1999
39. de Meijere, A.; Khlebnikov, A. F.; Suennemann, H. W.; Frank, D.; Rauch, K.; Yufit, D. S. Eur. J. Org. Chem. 2010, 17, 3295
40. Baron, O.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 3133
41. See also: Macdonald, J. E.; Poindexter, G. S. Tetrahedron Lett. 1987, 28, 1851
42. Lulinski, S.; Serwatowski, J. J. Org. Chem. 2003, 68, 9384
43. Chen, X.; Zhu, C.-J.; Guo, F.; Qiu, X.-W.; Yang, Y.-C.; Zhang, S.-Z.; He, M.-L.; Parveen, S.; Jing, C.-J.; Li, Y.; Ma, B. J. Med. Chem. 2010, 53, 8330
44. Dragovich, P.; Zhou, Y.; Webber, S. E. U.S. Patent US 2007/861678
45. Chem. Abstr. 2008, 149, 246568.
46. Balsubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 5, pp 245-300.
47. Mahalingam, A. K.; Wana, Y.; Murugaiah, A. M. S.; Wallinder, C.; Wua, X.; Plouffe, B.; Botros, M.; Nyberg, F.; Hallberg, A.; Gallo-Payet, N.; Alterman, M. Bioog. Med. Chem. 2010, 18, 4570
48. Lu, R.-J.; Tucker, J. A.; Zinevitch, T.; Kirichenko, O.; Konoplev, V.; Kuznetsova, S.; Sviridov, S.; Pickens, J.; Tandel, S.; Brahmachary, E.; Yang, Y.; Wang, J.; Freel, S.; Fisher, S.; Sullivan, A.; Zhou, J.; Stanfield-Oakley, S.; Greenberg, M.; Bolognesi, D.; Bray, B.; Koszalka, B.; Jeffs, P.; Khasanov, A.; Ma, Y.-A.; Jeffries, C.; Liu, C.; Proskurina, T.; Zhu, T.; Chucholowski, A.; Li, R.; Sexton, C. J. Med. Chem. 2007, 50, 6535
49. Taillier, C.; Hameury, T.; Bellosta, V.; Cossy, J. Tetrahedron 2007, 63, 4472
50. For metalation on 2- and 4-pyridinesulfonamides, see: Marsais, F.; Cronnier, A.; Trecourt, F.; Quéguiner, G. J. Org. Chem. 1987, 52, 1133
51. Breant, P.; Marsais, F.; Quéguiner, G. Synthesis 1983, 822
52. For metalation on 3-pyridinesulfonamides, see: Alo, B. I.; Familoni, O. B.; Marsais, F.; Quéguiner, G. J. Heterocycl. Chem. 1992, 29, 61
53. Kaiser, F.; Von Deyn, W.; Pohlman, M.; Bastiaans, H. M. M.; Anspaugh, D. D.; Culbertson, D. L.; Cotter, H. V. T. 2007, Appl. Int. WO2008/045588, 2007
54. Chem. Abstr. 2007, 146, 462247.
55. Alessi, M.; Larkin, A. L.; Olgivie, K. A.; Green, L. A.; Lai, S.; Lopez, S.; Snieckus, V. J. Org. Chem. 2007, 72, 1588
56. For commercial availability, see: http://www.combiphos.com/ and http://www.frontiersci.com/.
57. Tyrrell, E.; Brookes, P. Synthesis 2003, 469
58. Caron, S.; Hawkins, J. J. Org. Chem. 1998, 63, 2054
59. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
60. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633
61. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651
62. Anctil, E. J.-G.; Snieckus, V. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp 761-813.
63. Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150
64. -120 h for completion; see ref 6.
65. Review: Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366
66. Hurst, T. E.; Macklin, T. K.; Becker, M.; Hartman, E.; Kugel, W.; Parisienne-LaSalle, J.-C.; Batsanov, A.; Marder, T. B.; Snieckus, V. Chem.-Eur. J. 2010, 16, 8155
67. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
68. A single case of an unsymmetrical aryl diboronic ester prepared by Ir-catalyzed borylation has been reported; see: Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946