Palladium-catalysed dimerisation-distannylation of arynes: Synthesis and reaction of 2,2′-distannylbiaryls

Chemical Communications

Volumn , Issue 45, 2005, Pages 5678-5680

  Yoshida, Hiroto ^a   Tanino, Kenji ^a   Ohshita, Joji ^a   Kunai, Atsutaka ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PALLADIUM COMPLEX; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TIN; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DIMERIZATION; STOICHIOMETRY; SYNTHESIS;

EID: 28944446242     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511773a     Document Type: Article

References (46)

1. Reviews: G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;
2. S. P. Stanforth, Tetrahedron, 1998, 54, 263;
3. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz and M. Lemaire, Chem. Rev., 2002, 102, 1359.
4. Biaryl synthesis via oxidative couplings: G. Bringmann and S. Tasler, Tetrahedron, 2001, 57, 331;
5. H. Tohma, H. Morioka, S. Takizawa, M. Arisawa and Y. Kita, Tetrahedron, 2001, 57, 345;
6. R. Irie, K. Masutani and T. Katsuki, Synlett, 2000, 1433;
7. D. S. Surry, X. Su, D. J. Fox, V. Franckevicius, S. J. Macdonald and D. R. Spring, Angew. Chem., Int. Ed., 2005, 44, 1870.
8. H. Yoshida, Y. Honda, E. Shirakawa and T. Hiyama, Chem. Commun., 2001, 1880.
9. H. Yoshida, J. Ikadai, M. Shudo, J. Ohshita and A. Kunai, J. Am. Chem. Soc., 2003, 125, 6638;
10. H. Yoshida, J. Ikadai, M. Shudo, J. Ohshita and A. Kunai, Organometallics, 2005, 24, 156;
11. J. Ikadai, H. Yoshida, J. Ohshita and A. Kunai, Chem. Lett., 2005, 34, 56.
12. H. Yoshida, K. Tanino, J. Ohshita and A. Kunai, Angew. Chem., Int. Ed., 2004, 43, 5052.
13. We also reported synthesis of 1,2-disubstituted arenes through insertion reactions of arynes into a nucleophilic-electrophilic σ-bond: H. Yoshida, E. Shirakawa, Y. Honda and T. Hiyama, Angew. Chem., Int. Ed., 2002, 41, 3247;
14. H. Yoshida, T. Terayama, J. Ohshita and A. Kunai, Chem. Commun., 2004, 1980;
15. H. Yoshida, M. Watanabe, J. Ohshita and A. Kunai, Chem. Commun., 2005, 3292;
16. H. Yoshida, T. Minabe, J. Ohshita and A. Kunai, Chem. Commun., 2005, 3454.
17. Other catalytic transformations of arynes by use of a transition metal complex: E. Yoshikawa and Y. Yamamoto, Angew. Chem., Int. Ed., 2000, 39, 173;
18. E. Yoshikawa, K. V. Radhakrishnan and Y. Yamamoto, J. Am. Chem. Soc., 2000, 122, 7280;
19. N. Chatani, A. Kamitani, M. Oshita, Y. Fukumoto and S. Murai, J. Am. Chem. Soc., 2001, 123, 12686;
20. D. Peña, D. Pérez, E. Guitián and L. Castedo, Eur. J. Org. Chem., 2003, 7, 1238, and references cited therein.
21. Biaryl synthesis via aryne intermediates: H. Hart, K. Harada and C.-J. F. Du, J. Org. Chem., 1985, 50, 3104;
22. A. Saednya and H. Hart, Synthesis, 1996, 1455;
23. H. Tomori, J. M. Fox and S. L. Buchwald, J. Org. Chem, 2000, 65, 5334;
24. F. Leroux and M. Schlosser, Angew. Chem., Int. Ed., 2002, 41, 4272.
25. Y. Himeshima, T. Sonoda and H. Kobayashi, Chem. Lett., 1983, 1211.
26. A palladium-ETPO complex has been demonstrated by Tanaka to be an efficient catalyst for disilylation, digermylation, silylboration or stannylboration of such unsaturated organic compounds as alkynes and alkenes: H. Yamashita, M. Catellani and M. Tanaka, Chem. Lett., 1991, 241;
27. K. Mochida, C. Hodota, H. Yamashita and M. Tanaka, Chem. Lett., 1992, 1635;
28. S. Onozawa, Y. Hatanaka and M. Tanaka, Chem. Commun., 1997, 1229;
29. S. Onozawa, Y. Hatanaka and M. Tanaka, Chem. Commun., 1999, 1863;
30. S. Onozawa, Y. Hatanaka and M. Tanaka, Tetrahedron Lett., 1998, 39, 9043.
31. 3 gave an only 4% yield of the respective dimerisation-distannylation product.
32. We also examined an ETPO-type ligand bearing such a substituent as H, Me, Ph or t-Bu at its 4-position, however, none of them improved the yield and selectivity of 3a.
33. 2.
34. Although we also conducted the reactions of 3-methyl or 4-methoxybenzyne to investigate the regioselectivity in detail, both reactions resulted in the formation of a complex mixture.
35. Reviews: M. A. Bennett and H. P. Schwemlein, Angew. Chem., Int. Ed. Engl., 1989, 28, 1296;
36. M. A. Bennett and E. Wenger, Chem. Ber./Recl., 1997, 130, 1029.
37. B. L. Edelbach, D. A. Vicic, R. J. Lachicotte and W. D. Jones, Organometallics, 1998, 17, 4784;
38. B. L. Edelbach, R. J. Lachicotte and W. D. Jones, J. Am. Chem. Soc., 1998, 120, 2843;
39. T. Satoh and W. D. Jones, Organometallics, 2001, 20, 2916.
40. The reaction of a palladacyclopentadiene, derived from a Pd(0) complex and 2 mol of an alkyne, with an organostannane has been demonstrated to be a key step in the palladium-catalysed dimerisation-carbostannylation of alkynes: E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290;
41. H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637.
42. Copper(II)-promoted arylation of NH-containing compounds with organostannanes: P. Y. S. Lam, G. Vincent, D. Bonne and C. G. Clark, Tetrahedron Lett., 2002, 43, 3091.
43. Previously reported synthesis of 2,2′-distannylbiaryls: B. Schilling, V. Kaiser and D. E. Kaufmann, Chem. Ber./Recl., 1997, 130, 923;
44. T. Hoshi, H. Shionoiri, M. Katano, T. Suzuki, M. Ando and H. Hagiwara, Chem. Lett., 2002, 600;
45. T. Hoshi, H. Shionoiri, M. Katano, T. Suzuki and H. Hagiwara, Tetrahedron: Asymmetry, 2002, 13, 2167;
46. A. B. Chopa, M. T. Lochhart and G. F. Silbestri, Organometallics, 2002, 21, 5874.