Manganese-catalyzed phenylation of acetylenic compounds with a phenyl grignard reagent

Chemistry Letters

Volumn , Issue 1, 1998, Pages 11-12

  Yorimitsu, Hideki ^a   Tang, Jun ^a   Okada, Kenji ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032381578     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.11     Document Type: Article

References (14)

1. P. Knochel, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 4, Chap. 4.4, p. 865.
2. Phenylalumination of acetylene: J. J. Eisch, and W. C. Kaska, J. Am. Chem. Soc., 88, 2976 (1966); J. J. Eisch, R. Amtmann, and M. W. Foxton, J. Organomet. Chem. 16, P55 (1969); J. J. Eisch and R. Amtmann, J. Org, Chem., 37, 3410 (1972). Diarylation with aryltributylstannane: H. Oda, M. Morishita, K. Fugami, H. Sano, and M. Kosugi, Chem. Lett., 1996, 811. Ni-catalyzed phenylzincation: T. Stüdemann and P. Knochel, Angew. Chem., Int. Ed. Engl., 36, 93 (1997).
3. Phenylalumination of acetylene: J. J. Eisch, and W. C. Kaska, J. Am. Chem. Soc., 88, 2976 (1966); J. J. Eisch, R. Amtmann, and M. W. Foxton, J. Organomet. Chem. 16, P55 (1969); J. J. Eisch and R. Amtmann, J. Org, Chem., 37, 3410 (1972). Diarylation with aryltributylstannane: H. Oda, M. Morishita, K. Fugami, H. Sano, and M. Kosugi, Chem. Lett., 1996, 811. Ni-catalyzed phenylzincation: T. Stüdemann and P. Knochel, Angew. Chem., Int. Ed. Engl., 36, 93 (1997).
4. Phenylalumination of acetylene: J. J. Eisch, and W. C. Kaska, J. Am. Chem. Soc., 88, 2976 (1966); J. J. Eisch, R. Amtmann, and M. W. Foxton, J. Organomet. Chem. 16, P55 (1969); J. J. Eisch and R. Amtmann, J. Org, Chem., 37, 3410 (1972). Diarylation with aryltributylstannane: H. Oda, M. Morishita, K. Fugami, H. Sano, and M. Kosugi, Chem. Lett., 1996, 811. Ni-catalyzed phenylzincation: T. Stüdemann and P. Knochel, Angew. Chem., Int. Ed. Engl., 36, 93 (1997).
5. Phenylalumination of acetylene: J. J. Eisch, and W. C. Kaska, J. Am. Chem. Soc., 88, 2976 (1966); J. J. Eisch, R. Amtmann, and M. W. Foxton, J. Organomet. Chem. 16, P55 (1969); J. J. Eisch and R. Amtmann, J. Org, Chem., 37, 3410 (1972). Diarylation with aryltributylstannane: H. Oda, M. Morishita, K. Fugami, H. Sano, and M. Kosugi, Chem. Lett., 1996, 811. Ni-catalyzed phenylzincation: T. Stüdemann and P. Knochel, Angew. Chem., Int. Ed. Engl., 36, 93 (1997).
6. Phenylalumination of acetylene: J. J. Eisch, and W. C. Kaska, J. Am. Chem. Soc., 88, 2976 (1966); J. J. Eisch, R. Amtmann, and M. W. Foxton, J. Organomet. Chem. 16, P55 (1969); J. J. Eisch and R. Amtmann, J. Org, Chem., 37, 3410 (1972). Diarylation with aryltributylstannane: H. Oda, M. Morishita, K. Fugami, H. Sano, and M. Kosugi, Chem. Lett., 1996, 811. Ni-catalyzed phenylzincation: T. Stüdemann and P. Knochel, Angew. Chem., Int. Ed. Engl., 36, 93 (1997).
7. K. Okada, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 118, 6076 (1996); J. Tang, K. Okada, H. Shinokubo, and K. Oshima, Tetrahedron, 53, 5061 (1997).
8. K. Okada, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 118, 6076 (1996); J. Tang, K. Okada, H. Shinokubo, and K. Oshima, Tetrahedron, 53, 5061 (1997).
9. H. Westmijze, H. Kleijn, and P. Vermeer, Tetrahedron Lett., 1977, 2023.
10. Prepared from 1-octyne and iodobenzene derivatives: K. Sonogashira, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, Chap. 2.4, p. 521.
11. 29N: C, 85.94; H, 9.51%.
12. 26O: C, 85.66; H, 8.90%.
13. Although the precise mechanism to account for the results of entries 1-10 remains unclear, we assume that the electronic effect of substituents on benzene ring should play an important role.
14. The reaction of 5c with other Grignard reagent such as p-methoxyphenylmagnesium bromide or 1-naphthyl-magnesium bromide provided the corresponding adduct in 50% or 25% yield, respectively along with the recovered starting material (35% or 63%). The use of 2-thienylmagnesium bromide resulted in complete recovery of 5c.