Fourfold Suzuki-Miyaura and Sonogashira cross-coupling reactions on tetrahedral methane and adamantane derivatives

European Journal of Organic Chemistry

Volumn , Issue 9, 2011, Pages 1743-1754

  Schilling, Christine I ^a   Plietzsch, Oliver ^a   Nieger, Martin ^b   Muller, Thierry ^a   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Adamantane; Cross coupling; Hydrocarbons; Molecular tecton; Organic building unit

Indexed keywords

EID: 79952503951     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001567     Document Type: Article

References (67)

1. O. Ermer, J. Am. Chem. Soc. 1988, 110, 3747-3754.
2. J.-H. Fournier, T. Mairs, J. D. Wuest, J. Org. Chem. 2004, 69, 1762-1775.
3. J. Kim, B. Chen, T. M. Reineke, H. Li, M. Eddaoudi, D. B. Moler, M. O'Keeffe, O. M. Yaghi, J. Am. Chem. Soc. 2001, 123, 8239-8247.
4. M. Wind, K. Saalwächter, U.-M. Wiesler, K. Müllen, H. W. Spiess, Macromolecules 2002, 35, 10071-10086.
5. C. G. Clark, R. J. Wenzel, E. V. Andreitchenko, W. Steffen, R. Zenobi, K. Müllen, New J. Chem. 2007, 31, 1300-1306.
6. P. Kuhn, M. Antonietti, A. Thomas, Angew. Chem. 2008, 120, 3499;
7. Angew. Chem. Int. Ed. 2008, 47, 3450-3453.
8. H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortés, A. P. Côté, R. E. Taylor, M. O'Keeffe, O. M. Yaghi, Science 2007, 316, 268-272.
9. F. J. Uribe-Romo, J. R. Hunt, H. Furukawa, C. Klöck, M. O'Keeffe, O. M. Yaghi, J. Am. Chem. Soc. 2009, 131, 4570-4571.
10. O. Plietzsch, C. I. Schilling, M. Tolev, M. Nieger, C. Richert, T. Muller, S. Bräse, Org. Biomol. Chem. 2009, 7, 4734-4743.
11. M. Janssen, C. Müller, D. Vogt, Adv. Synth. Catal. 2010, 351, 313-318.
12. D. Laliberté, T. Maris, J. D. Wuest, Can. J. Chem. 2004, 82, 386-398.
13. O. Plietzsch, C. I. Schilling, T. Muller, S. Bräse, Tetrahedron: Asymmetry 2010, 21, 1474-1479.
14. I. Oesterling, K. Müllen, J. Am. Chem. Soc. 2007, 129, 4595-4605.
15. T. Qin, G. Zhou, H. Schreiber, R. E. Bauer, M. Baumgarten, C. E. Anson, E. J. W. List, K. Müllen, Angew. Chem. 2008, 120, 8416;
16. Angew. Chem. Int. Ed. 2008, 47, 8292-8296.
17. E. V. Andreitchenko, R. E. Bauer, C. Kreutz, M. Baumgarten, J. Bargon, K. Müllen, Macromolecules 2008, 41, 548-558.
18. E. C. Constable, O. Eich, C. E. Housecroft, L. A. Johnston, Chem. Commun. 1998, 2661-2662.
19. E. C. Constable, C. E. Housecroft, J. Chem. Soc., Dalton Trans. 1999, 1363-1364.
20. For fourfold Suzuki-Miyaura reactions, see
21. L. J. Mathias, V. R. Reichert, A. V. G. Muir, Chem. Mater. 1993, 5, 4-5.
22. L. M. Wilson, A. C. Griffin, J. Mater. Chem. 1993, 3, 991-994.
23. V. R. Reichert, L. J. Mathias, Macromolecules 1994, 27, 7015-7023.
24. S. Wang, W. J. Oldham Jr., R. A. Hudack Jr., G. C. Bazan, J. Am. Chem. Soc. 2000, 122, 5695-5709.
25. J. Pei, J. Ni, X.-H. Zhou, X.-Y. Cao, Y.-H. Lai, J. Org. Chem. 2002, 67, 4924-4936.
26. C. S. Krämer, T. J. Zimmermann, M. Sailer, T. J. J. Müller, Synthesis 2002, 1163-1170.
27. X.-M. Liu, C. He, X.-T. Hao, L.-W. Tan, Y. Li, K. S. Ong, Macromolecules 2004, 37, 5965-5970.
28. D.-R. Bai, S. Wang, Organometallics 2004, 23, 5958-5966.
29. S. Kotha, M. Behera, Indian J. Chem. 2006, 45B, 2684-2689.
30. S. Jeeva, S. C. Moratti, Synthesis 2007, 3323-3328.
31. J. Schmidt, J. Weber, J. D. Epping, M. Antionietti, A. Thomas, Adv. Mater. 2009, 21, 702-705.
32. T. Bauer, A. D. Schlüter, J. Sakamoto, Synlett 2010, 877-880. for fourfold Sonogashira reactions, see
33. E. Galoppini, R. Gilardi, Chem. Commun. 1999, 173-174.
34. M. Simard, D. Su, J. D. Wuest, J. Am. Chem. Soc. 1991, 113, 4696-4698.
35. V. E. Reichert, L. J. Mathias, Macromolecules 1994, 27, 7030-7034.
36. D. Su, X. Wang, M. Simard, J. D. Wuest, Supramol. Chem. 1995, 6, 171-178.
37. B. Gõmez-Lor, A. M. Echavarren, A. Santos, Tetrahedron Lett. 1997, 38, 5347-5350.
38. E. C. Constable, O. Eich, D. Fenske, C. E. Housecroft, L. A. Johnston, Chem. Eur. J. 2000, 6, 4364-4370.
39. W. Guo, E. Galoppini, R. Gilardi, G. I. Rydja, Y.-H. Chen, Cryst. Growth Des. 2001, 1, 231-237.
40. I. Aujard, J.-P. Baltaze, J.-B. Baudin, E. Cogné, F. Ferrage, L. Jullien, É. Perez, V. Prévost, L. M. Qian, O. Ruel, J. Am. Chem. Soc. 2001, 123, 8177-8188.
41. R. E. Bauer, V. Enkelmann, U. M. Wiesler, A. J. Berresheim, K. Müllen, Chem. Eur. J. 2002, 8, 3858-3864.
42. Q. Li, A. V. Rukavishnikov, P. A. Petukhov, T. O. Zaikova, J. F. W. Keana, Org. Lett. 2002, 4, 3631-3634.
43. Q. Li, A. V. Rukavishnikov, P. A. Petukhov, T. O. Zaikova, C. Jin, J. F. W. Keana, J. Org. Chem. 2003, 68, 4862-4869.
44. A. Enzmann, W. Beck, Z. Naturforsch., B: J. Chem. Sci. 2004, 59, 865-868.
45. Y. Kuramochi, A. Satake, Y. Kobuke, J. Am. Chem. Soc. 2004, 126, 8668-8669.
46. D. Schindler, F. Eißman, E. Weber, Org. Biomol. Chem. 2009, 7, 3549-3560.
47. S. Yuan, S. Kirklin, B. Donrey, D.-J. Liu, L. Yu, Macromolecules 2009, 42, 1554-1559; for fourfold Mizoroki-Heck reaction, see
48. W. J. Oldham Jr., R. J. Lachicotte, G. C. Bazan, J. Am. Chem. Soc. 1998, 120, 2987-2988.
49. S. Sengupta, S. K. Sadhukhan, Tetrahedron Lett. 1999, 40, 9157-9161.
50. T. J. Zimmermann, T. J. J. Müller, Eur. J. Org. Chem. 2002, 2269-2279. for examples of other fourfold cross-couplings, see
51. R. Rathore, C. L. Burns, M. I. Deselnicu, Org. Lett. 2001, 3, 2887-2890.
52. X.-M. Liu, C. He, J. Huang, J. Xu, Chem.Mater. 2005, 17, 434-441.
53. J. Schmidt, M. Werner, A. Thomas, Macromolecules 2009, 42, 4426-4429.
54. W. Lu, D. Yuan, D. Zhao, C. I. Schilling, O. Plietzsch, T. Muller, S. Bräse, J. Guenther, J. Blümel, R. Krishna, Z. Li, H.-C. Zhou, Chem. Mater. 2010, 22, 5964-5972.
55. T. Ben, H. Ren, S. Ma, D. Cao, J. Lan, X. Jing, W. Wang, J. Xu, F. Deng, J. M. Simmons, S. Qiu, G. Zhu, Angew. Chem. 2009, 121, 9621;
56. Angew. Chem. Int. Ed. 2009, 48, 9457-9460.
57. J. R. Holst, E. Stöckel, D. J. Adams, A. I. Cooper, Macromolecules 2010, 43, 8531-8538.
58. [5,8,10] and
59. M. Meng, C. Ahlborn, M. Bauer, O. Plietzsch, S. A. Soomro, A. Singh, T. Muller, W. Wenzel, S. Bräse, C. Richert, ChemBioChem 2009, 10, 1335-1339. for work on fullerene-based building blocks, see
60. A. J. Inglis, P. Pierrat, T. Muller, S. Bräse, C. Barner-Kowollik, Soft Mater. 2010, 6, 82-84.
61. P. Pierrat, C. Réthoré, T. Muller, S. Bräse, Chem. Eur. J. 2009, 15, 11458-11460.
62. P. Pierrat, S. Vanderheiden, T. Muller, S. Bräse, Chem. Commun. 2009, 1748-1750.
63. P. Pierrat, C. Réthoré, T. Muller, S. Bräse, Synlett 2008, 1706-1710.
64. C. Lambert, W. Gaschler, G. Nöll, M. Weber, E. Schmälzlin, J. Chem. Soc. Perkin Trans. 2 2001, 964-974.
65. Y. Kuramochi, A. Satake, M. Itou, K. Ogawa, Y. Araki, O. Ito, Y. Kobuke, Chem. Eur. J. 2008, 14, 2827-2841.
66. Y. Liu, X. Xu, F. Zheng, Y. Cui, Angew. Chem. 2008, 120, 4614;
67. Angew. Chem. Int. Ed. 2008, 47, 4538-4541.