A new convenient synthesis of triarylbismuthanes bearing three different aryl groups by the grignard arylation of unsymmetrical diarylbismuth triflate-hexamethylphosphoric triamide (HMPA) complexes

Organometallics

Volumn 15, Issue 7, 1996, Pages 1951-1953

  Matano, Yoshihiro ^a   Miyamatsu, Takashi ^a   Suzuki, Hitomi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000153329     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9509709     Document Type: Article

References (17)

1. ArAr′Ar″Bi type of compounds: (a) Bras, P.; Van Der Gen, A.; Wolters, J. J. Organomet. Chem. 1983, 256, C1. (b) Suzuki, H.; Murafuji, T. J. Chem. Soc., Chem. Commun. 1992, 1143.
2. ArAr′Ar″Bi type of compounds: (a) Bras, P.; Van Der Gen, A.; Wolters, J. J. Organomet. Chem. 1983, 256, C1. (b) Suzuki, H.; Murafuji, T. J. Chem. Soc., Chem. Commun. 1992, 1143.
3. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
4. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
5. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
6. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
7. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
8. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
9. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
10. ArAr′BiX (X = halogen or oxygen) type of compounds: (a) Bras, P.; Herwijer, H.; Wolters, J. J. Organomet. Chem. 1981, 212, C7. (b) Yamamoto, Y.; Chen, X.; Kojima, S.; Ohdoi, S.; Kitano, M.; Doi, Y.; Akiba, K.-y. J. Am. Chem. Soc. 1995, 117, 3922. Chen, X.; Ohdoi, K.; Yamamoto, Y.; Akiba, K.-y. Organometallics 1993, 12, 1857. (d) Yamamoto, Y.; Chen, X.; Akiba, K.-y. J. Am. Chem. Soc. 1992, 114, 7906. (e) Chen, X.; Yamamoto, Y.; Akiba, K.-y.; Yoshida, S.; Yasui, M.; Iwasaki, F. Tetrahedron Lett. 1992, 33, 6653. (f) Murafuji, T.; Mutoh, T.; Satoh, K.; Tsunenari, K.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 3848. (g) Murafuji, T.; Azuma, N.; Suzuki, H. Organometallics 1995, 14, 1542. (h) Suzuki, H.; Murafuji, T.; Matano, Y.; Azuma, Y. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
11. For a review, see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982, 82, 15.
12. 3 in diethyl ether for 5 h at room temperature gave the corresponding diarylbismuth chloride, arylbismuth dichloride, and unreacted bismuthane in the ratio 74:7:19.
13. (a) Carmalt, C. J.; Norman, N. C.; Orpen, A. G.; Stratford, S. E. J. Organomet. Chem. 1993, 460, C22.
14. (b) Carmalt, C. J.; Cowley, A. W.; Decken, A.; Norman, N. C. J. Organomet. Chem. 1995, 496, 59.
15. (c) Clegg, W.; Elsegood, M. R. J.; Errington, R. J.; Fisher, G. A.; Norman, N. C. J. Mater. Chem. 1994, 891.
16. (d) Clegg, W.; Errington, R. J.; Fisher, G. A.; Flynn, R. J.; Norman, N. C. J. Chem. Soc., Dalton Trans. 1993, 637.
17. (e) Clegg, W.; Errington, R. J.; Fisher, G. A.; Hockless, D. C. R.; Norman, N. C.; Orpen, A. G.; Stratford, S. E. J. Chem. Soc., Dalton Trans. 1992, 1967.