Suzuki-miyaura cross coupling reactions of b-Allenyl-9-BBN

Chemistry Letters

Volumn 40, Issue 9, 2011, Pages 950-952

  Radkowski, Karin ^a   Seidel, Günter ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80052589052     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.950     Document Type: Article

References (51)

1. Modern Allene Chemistry, ed. by N. Krause, A. S. K. Hashmi, Wiley-VCH, Weinheim, 2004, Vols. 1 and 2.
2. A. Hoffmann-Röder, N. Krause, Angew. Chem., Int. Ed. 2004, 43, 1196.
3. H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley, New York, 1984.
4. S. Ma, Chem. Rev. 2005, 105, 2829.
5. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994.
6. A. Fürstner, P. W. Davies, Angew. Chem., Int. Ed. 2007, 46, 3410.
7. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395.
8. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326.
9. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180.
10. For studies on φ-acid-catalyzed reactions of allenes reported by our group, see: H. Teller, S. Flügge, R. Goddard, A. Fürstner, Angew. Chem., Int. Ed. 2010, 49, 1949.
11. M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem., Int. Ed. 2010, 49, 2542.
12. V. Mamane, P. Hannen, A. Fürstner, Chem.-Eur. J. 2004, 10, 4556.
13. O. Lepage, E. Kattnig, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 15970.
14. A. Larivée, J. B. Unger, M. Thomas, C. Wirtz, C. Dubost, S. Handa, A. Fürstner, Angew. Chem., Int. Ed. 2011, 50, 304.
15. A. Fürstner, M. Méndez, Angew. Chem., Int. Ed. 2003, 42, 5355.
16. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., ed. by A. de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004, Vols. 1 and 2.
17. Cross-Coupling Reactions: A Practical Guide in Topics in Current Chemistry, ed. by N. Miyaura, Springer, Berlin, 2002, Vol. 219. doi:10.1007/3- 540-45313-X.
18. Handbook of Organopalladium Chemistry for Organic Synthesis, ed. by E. Negishi, Wiley, New York, 2002.
19. In the context of this study, it is important to note that boronic acid derivatives are known to add to allenes under fairly mild conditions in the presence of palladium catalysts, see: M. Yoshida, K. Matsuda, Y. Shoji, T. Gotou, M. Ihara, K. Shishido, Org. Lett. 2008, 10, 5183.
20. H. Guo, S. Ma, Synthesis 2007, 2731.
21. In response to these challenges, alternative procedures using nonmetallic three carbon-donors were recently developed for the preparation of arylallenes. For leading examples, see: S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2008, 130, 5048.
22. H. Nakamura, T. Kamakura, S. Onagi, Org. Lett. 2006, 8, 2095.
23. H. Nakamura, M. Ishikura, T. Sugiishi, T. Kamakura, J.-F. Biellmann, Org. Biomol. Chem. 2008, 6, 1471, and literature therein.
24. R. H. Kleijn, J. Meijer, E. A. Oostveen, P. Vermeer, J. Organomet. Chem. 1982, 224, 399.
25. C. E. Russell, L. S. Hegedus, J. Am. Chem. Soc. 1983, 105, 943.
26. W. de Graaf, J. Boersma, G. van Koten, C. J. Elsevier, J. Organomet. Chem. 1989, 378, 115.
27. S. Ma, A. Zhang, J. Org. Chem. 1998, 63, 9601.
28. K. Lee, D. Seomoon, P. H. Lee, Angew. Chem., Int. Ed. 2002, 41, 3901.
29. P. H. Lee, J. Mo, D. Kang, D. Eom, C. Park, C.-H. Lee, Y. M. Jung, H. Hwang, J. Org. Chem. 2011, 76, 312.
30. I. S. Aidhen, R. Braslau, Synth. Commun. 1994, 24, 789.
31. D. Badone, R. Cardamone, U. Guzzi, Tetrahedron Lett. 1994, 35, 5477.
32. C.-W. Huang, M. Shanmugasundaram, H.-M. Chang, C.-H. Cheng, Tetrahedron 2003, 59, 3635.
33. S. Rousset, M. Abarbri, J. Thibonnet, A. Duchêne, J.-L. Parrain, Chem. Commun. 2000, 1987.
34. C. Mukai, Y. Takahashi, Org. Lett. 2005, 7, 5793.
35. K. Cherry, A. Duchêne, J. Thibonnet, J.-L. Parrain, M. Abarbri, Synthesis 2005, 2349.
36. D. R. Williams, A. A. Shah, Chem. Commun. 2010, 46, 4297.
37. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
38. A. Suzuki, J. Organomet. Chem. 1999, 576, 147.
39. O. B. Locos, K. Dahms, M. O. Senge, Tetrahedron Lett. 2009, 50, 2566.
40. A. Fürstner, G. Seidel, Tetrahedron 1995, 51, 11165.
41. A. Fürstner, G. Seidel, Synlett 1998, 161.
42. For advanced applications, see: S. Benson, M.-P. Collin, G. W. O'Neil, J. Ceccon, B. Fasching, M. D. B. Fenster, C. Godbout, K. Radkowski, R. Goddard, A. Fürstner, Angew. Chem., Int. Ed. 2009, 48, 9946.
43. A. Fürstner, C. Nevado, M. Waser, M. Tremblay, C. Chevrier, F. Teplý, C. Aïssa, E. Moulin, O. Müller, J. Am. Chem. Soc. 2007, 129, 9150.
44. A. Fürstner, E. Kattnig, O. Lepage, J. Am. Chem. Soc. 2006, 128, 9194.
45. A. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2006, 128, 8087.
46. A. Fürstner, G. Seidel, J. Org. Chem. 1997, 62, 2332.
47. G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275.
48. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685.
49. A. Fürstner, A. Leitner, Synlett 2001, 290.
50. H. C. Brown, U. R. Khire, G. Narla, U. S. Racherla, J. Org. Chem. 1995, 60, 544.
51. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/ index.html.