Palladium-catalyzed cross-coupling reaction of thioglycosides with (hetero)aryl halides

Advanced Synthesis and Catalysis

Volumn 355, Issue 2-3, 2013, Pages 477-490

  Brachet, Etienne ^a   Brion, Jean Daniel ^a   Messaoudi, Samir ^a   Alami, Mouad ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

(hetero)aryl halides; C S bond formation; Palladium catalysis; Thioglycosides

Indexed keywords

EID: 84875718522     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200695     Document Type: Article

References (71)

1. For general reviews, see: a) H. Driguez, Thiooligosaccharides in glycobiology. Glycoscience Synthesis of Substrate Analogs and Mimetics, in: Topics in Current Chemistry, Springer, Berlin, Vol. 187, pp 85-116, 1997
2. Z. J. Witczak, Curr. Med. Chem. 1999, 6, 165-178
3. K. Pachamuthu, R. R. Schmidt, Chem. Rev. 2006, 106, 160-187
4. M. Samuni-Blank, I. Izhaki, M. D. Dearing, Y. Gerchman, B. Trabelcy, A. L. W. H. Karasov, Z. Arad, Curr. Biol. 2012, 22, 1218-1220.
5. C. S. Rye, S. G. Withers, Carbohydr. Res. 2004, 339, 699-703
6. B. B. Metaferia, B. J. Fetterolf, S. Shazadul-Hussan, M. Moravec, J. A. Smith, S. Ray, M.-T. Gutierrez-Lugo, C. A. Bewley, J. Med. Chem. 2007, 50, 6326-6336
7. F. Castaneda, A. Burse, W. Boland, R. K.-H. Kinne, Int. J. Med. Sci. 2007, 4, 131-139.
8. R. Furneaux, R. Ferrier, Methods Carbohydr. Chem. 1980, 8, 251-253
9. K. C. Nicolaou, J. L. Randall, G. T. Furst, J. Am. Chem. Soc. 1985, 107, 5556-5558
10. S. K. Das, J. Roy, K. A. Reddy, C. Abbineni, Carbohydr. Res. 2003, 338, 2237-2240
11. C.-A. Tai, S. S. Kulkarni, S.-C. Hung, J. Org. Chem. 2003, 68, 8719-8722
12. C.-A. Tai, S. S. Kulkarni, S. C. Hung, J. Org. Chem. 2003, 68, 8719-8722
13. S. K. Das, J. Roy, K. A. Reddy, C. Abbineni, Carbohydr. Res. 2003, 338, 2237-2240
14. G. Agnihotri, P. Tiwari, A. K. Misra, Carbohydr. Res. 2005, 340, 1393-1396.
15. E. Fischer, K. Delbruek, Ber. Dtsch. Chem. Ges. 1909, 42, 1476-1482
16. M. Blanc-Muesser, J. Defaye, H. Driguez, Carbohydr. Res. 1978, 67, 305-328
17. M. Apparu, M. Blanc-Muesser, J. Defaye, H. Driguez, Can. J. Chem. 1981, 59, 314-320.
18. S-S. Weng, Y-D. Lin, C-T. Chen, Org. Lett. 2006, 8, 5633-5636.
19. P. Naus, L. Leseticky, S. Smrcek, I. Tislerova, M. Sticha, Synlett 2003, 2117-2122.
20. 2 (1.5 equiv.) in DMF at elevated temperature (153 °C). The yield of the formed product was moderate (51%), but no spectral data are available in the supporting information, see: P. S. Herradura, K. A. Pendola, R. K. Guy, Org. Lett. 2000, 2, 2019-2022.
21. D. Audisio, S. Messaoudi, J.-F. Peyrat, J.-D. Brion, M. Alami, Tetrahedron Lett. 2007, 48, 6928-6932
22. S. Messaoudi, D. Audisio, J.-D. Brion, M. Alami, Tetrahedron 2007, 63, 10202-10210
23. D. Audisio, S. Messaoudi, J.-F. Peyrat, J.-D. Brion, M. Alami, J. Org. Chem. 2011, 76, 4995-5005
24. M. A. Soussi, D. Audisio, S. Messaoudi, O. Provot, J.-D. Brion, M. Alami, Eur. J. Org. Chem. 2011, 5077-5088.
25. Selected representative examples for the Pd-catalyzed C-S cross-coupling reaction see: a) T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, M. Kosugi, Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389
26. U. Schopfer, A. Schlapbach, Tetrahedron 2001, 57, 3069-3073
27. G. Y. Li, G. Zheng, A. F. Noonan, J. Org. Chem. 2001, 66, 8677-8688
28. M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397-7403
29. T. Itoh, T. Mase, Org. Lett. 2004, 6, 4587-4590
30. M. A. Fernandez-Rodroeguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180-2181
31. M. A. Fernandez-Rodroeguez, Q. Shen, J. F. Hartwig, Chem. Eur. J. 2006, 12, 7782-7796
32. C. C. Eichman, J. P. Stambuli, J. Org. Chem. 2009, 74, 4005-4008
33. M. A. Fernández-Rodríguez, J. F. Hartwig, J. Org. Chem. 2009, 74, 1663-1672
34. C. Bryan, J. Braunger, M. Lautens, Angew. Chem. 2009, 121, 7198-7202
35. Angew. Chem. Int. Ed. 2009, 48, 7064-7068
36. M. Fernández-Rodríguez, J. Hartwig, Chem. Eur. J. 2010, 16, 2355-2359
37. A. van den Hoogenband, J. W. Lange, R. P. Bronger, A. R. Stoit, S. W. Tupstra, Tetrahedron Lett. 2010, 51, 6877-6881.
38. K. C. Kong, C. H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313-63155
39. L. Pellegatti, E. Vedrenne, J.-M. Leger, C. Jarry, S. Routier, J. Comb. Chem. 2010, 12, 604-608
40. S. Messaoudi, J.-D. Brion, M. Alami, Org. Lett. 2012, 14, 1496-1499.
41. For C-S bond forming reaction from N-tosylhydrazones, see: a) Q. Ding, B. Cao, J. Yuan, X. Liu, Y. Peng, Org. Biomol. Chem. 2011, 9, 748-751
42. X.-W. Feng, J. Wang, J. Zhang, J. Yang, N. Wang, X.-Q. Yu, Org. Lett. 2010, 12, 4408-4411
43. J. Barluenga, M. Tomas-Gamasa, F. Aznar, C. Valdes, Eur. J. Org. Chem. 2011, 1520-1526.
44. For selected examples of C-C bond forming reaction from N-tosylhydrazones, see: a) J. Barluenga, P. Moriel, C. Valdes, F. Aznar, Angew. Chem. 2007, 119, 5683-5686
45. Angew. Chem. Int. Ed. 2007, 46, 5587-5590
46. W.-Y. Yu, Y.-T. Tsoi, Z. Zhou, A. S. C. Chan, Org. Lett. 2009, 11, 469-472
47. J. Barluenga, M. Tomas-Gamasa, F. Aznar, C. Valdes, Chem. Eur. J. 2010, 16, 12801-12803
48. B. Tréguier, A. Hamze, O. Provot, J.- D. Brion, M. Alami, Tetrahedron Lett. 2009, 50, 6549-6552
49. X. Zhao, J. Jing, K. Lu, Y. Zhang, J. Wang, Chem. Commun. 2010, 46, 1724-1726
50. E. Brachet, A. Hamze, J.-F. Peyrat, J.-D. Brion, M. Alami, Org. Lett. 2010, 12, 4042-4045
51. X. Zhao, G. Wu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 3296-3299.
52. For C-O bond forming reaction, see: h) J. Barluenga, M. Tomas-Gamasa, F. Aznar, C. Valdes, Angew. Chem. 2010, 122, 5113-5116
53. Angew. Chem. Int. Ed. 2010, 49, 4993-4996
54. for C-N bond forming reaction, see: i) A. Hamze, B. Tréguier, J.-D. Brion, M. Alami, Org. Biomol. Chem. 2011, 9, 6200-6204.
55. L. Salvi, N. R. Davis, S. Z. Ali, S. L. Buchwald, Org. Lett. 2012, 14, 170-173
56. K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 10694-10695
57. A. V. Vorogushin, X. Huang, S. L. Buchwald J. Am. Chem. Soc. 2005, 127, 8146-8149.
58. S. Messaoudi, B. Tréguier, A. Hamze, O. Provot, J.-F. Peyrat, J. R. Rodrigo De Losada, J.-M. Liu, J. Bignon, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, J. Med. Chem. 2009, 52, 4538-4542
59. A. Hamze, A. Giraud, S. Messaoudi, O. Provot, J.-F. Peyrat, J. Bignon, J.-M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, ChemMed-Chem 2009, 4, 1912-1924
60. A. Hamze, E. Rasolfonjatovo, O. Provot, C. Mousset, D. Veau, J. Rodrigo, J. Bignon, J.-M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, ChemMedChem 2011, 6, 2179-2191.
61. G. R. Pettit, B. Toki, D. L. Herald, P. Verdier-Pinard, M. R. Boyd, E. Hamel, R. K. Pettit, J. Med. Chem. 1998, 41, 1688-1695
62. J.-P. Liou, J.-Y. Chang, C.-W. Chang, C.-Y. Chang, N. Mahindroo, F.-M. Kuo, H.-P. Hsieh, J. Med. Chem. 2004, 47, 2897-2905.
63. D. Audisio, S. Messaoudi, L. Ceigeikowski, J.-F. Peyrat, J.-D. Brion, D. Methy-Gonnot, C. Radanyi, J.-M. Renoir, M. Alami, ChemMedChem 2011, 6, 804-815.
64. B. K. Barr, R. J. Holewinski, Biochemistry 2002, 41, 4447-4452.
65. C. Bao, G. Fan, Q. Lin, B. Li, S. Cheng, Q. Huang, L. Zhu, Org. Lett. 2012, 14, 572-575.
66. N. Floyd, B. Vijayakrishnan, J. R. Koeppe, B. G. Davis, Angew. Chem. 2009, 121, 7938-7942
67. Angew. Chem. Int. Ed. 2009, 48, 7798-7802.
68. G. J. L. Bernardes, D. P. Gamblin, B. G. Davis, Angew. Chem. 2006, 118, 4111-4115
69. Angew. Chem. Int. Ed. 2006, 45, 4007-4011.
70. M. Gao, Y. Chen, S. Tan, J. H. Reibenspies, R. A. Zingaro, Heteroat. Chem. 2008, 19, 199-206.