Consecutive cross-coupling of o-phenylenedizinc compound with acyl and/or aryl halides in the presence of Pd(0)-tris(2,4,6- trimethoxyphenyl)phosphine

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4629-4632

  Saiga, Akihiro ^a   Hossain, Kabir M ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Coupling reactions; Palladium and compounds; Polyaryls; Zinc and compounds

Indexed keywords

2 PHENYLENEDIZINC DERIVATIVE; HALIDE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; TRIS(2,4,6 TRIMETHOXYPHENYL)PHOSPHINE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034640897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00679-1     Document Type: Article

References (19)

1. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
2. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
3. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
4. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
5. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
6. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
7. For recent examples, see: (a) Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959. (b) Rottlander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573. (c) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901. (d) Haley, M. H.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. (e) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455. (f) Balavoine, F.; Madec, D.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8351. (g) Bowles, D. M.; Anthony, J. E. Organic Lett. 2000, 2, 85.
8. Okano, M.; Amano, M.; Takagi, K. Tetrahedron Lett. 1998, 39, 3001 and references cited therein.
9. Takagi, K.; Shimoishi, Y.; Sasaki, K. Chem. Lett. 1994, 2055 and references cited therein.
10. Goedheijt, M. S.; Nijbacker, T.; Akkerman, O. S.; Bickelhaupt, F.; Veldman, N.; Spek, A. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1550.
11. Amano, M.; Saiga, A.; Ikegami, R.; Ogata, T.; Takagi, K. Tetrahedron Lett. 1998, 39, 8667.
12. For the introduction of two different electrophiles onto the adjacent carbons of the benzene, pyridine, thiophene, or pyrolle ring via the stepwise generation of organometallic compounds followed by the treatment with electrophilic reagents at one reaction center and then at another reaction center, see: (a) Takahashi, M.; Hatano, K.; Kawada, Y.; Koga, G.; Tokitoh, N.; Okazaki, R. Chem. Commun. 1993, 1850. (b) Takahashi, M.; Hatano, K.; Kimura, M.; Watanabe, T.; Oriyama, T.; Koga, G. Tetrahedron Lett. 1994, 35, 579. (c) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565. (d) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993. (e) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
13. For the introduction of two different electrophiles onto the adjacent carbons of the benzene, pyridine, thiophene, or pyrolle ring via the stepwise generation of organometallic compounds followed by the treatment with electrophilic reagents at one reaction center and then at another reaction center, see: (a) Takahashi, M.; Hatano, K.; Kawada, Y.; Koga, G.; Tokitoh, N.; Okazaki, R. Chem. Commun. 1993, 1850. (b) Takahashi, M.; Hatano, K.; Kimura, M.; Watanabe, T.; Oriyama, T.; Koga, G. Tetrahedron Lett. 1994, 35, 579. (c) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565. (d) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993. (e) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
14. For the introduction of two different electrophiles onto the adjacent carbons of the benzene, pyridine, thiophene, or pyrolle ring via the stepwise generation of organometallic compounds followed by the treatment with electrophilic reagents at one reaction center and then at another reaction center, see: (a) Takahashi, M.; Hatano, K.; Kawada, Y.; Koga, G.; Tokitoh, N.; Okazaki, R. Chem. Commun. 1993, 1850. (b) Takahashi, M.; Hatano, K.; Kimura, M.; Watanabe, T.; Oriyama, T.; Koga, G. Tetrahedron Lett. 1994, 35, 579. (c) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565. (d) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993. (e) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
15. For the introduction of two different electrophiles onto the adjacent carbons of the benzene, pyridine, thiophene, or pyrolle ring via the stepwise generation of organometallic compounds followed by the treatment with electrophilic reagents at one reaction center and then at another reaction center, see: (a) Takahashi, M.; Hatano, K.; Kawada, Y.; Koga, G.; Tokitoh, N.; Okazaki, R. Chem. Commun. 1993, 1850. (b) Takahashi, M.; Hatano, K.; Kimura, M.; Watanabe, T.; Oriyama, T.; Koga, G. Tetrahedron Lett. 1994, 35, 579. (c) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565. (d) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993. (e) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
16. For the introduction of two different electrophiles onto the adjacent carbons of the benzene, pyridine, thiophene, or pyrolle ring via the stepwise generation of organometallic compounds followed by the treatment with electrophilic reagents at one reaction center and then at another reaction center, see: (a) Takahashi, M.; Hatano, K.; Kawada, Y.; Koga, G.; Tokitoh, N.; Okazaki, R. Chem. Commun. 1993, 1850. (b) Takahashi, M.; Hatano, K.; Kimura, M.; Watanabe, T.; Oriyama, T.; Koga, G. Tetrahedron Lett. 1994, 35, 579. (c) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565. (d) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993. (e) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
17. Frid, M.; Perez, D.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9469.
18. The present results are far from satisfactory because the purification of the intermediary compound 6, prior to the treatment with the second electrophiles, is not possible from a practical point of view.
19. Yields of 3a and 4a (utilized ligand): 35, 26 (tris(perfluorophenyl)phosphine); 75, 6 (tris(2-trifluoromethylphenyl)phosphine); 48, 15 (tri-2-furylphosphine); 62, 15 (triphenylarsine) 91, 2 (tri(o-tolyl)phosphine). A very different effect of ligands was observed in the Pd(0)-catalyzed stepwise reaction of bis(iodozincio)methane with two different electrophiles. See: Utimoto, K.; Toda, N.; Mizuno, T.; Kobata, M.; Matsubara, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2804.