Manganese-catalyzed carbomagnesation of alkynes

Catalysis Surveys from Asia

Volumn 7, Issue 1, 2003, Pages 39-46

  Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkyne; Carbometallation; Cyclization; Grignard reagent; Manganese

Indexed keywords

ALKYL GROUP; ALKYNE DERIVATIVE; ALLYL COMPOUND; MANGANESE; NITROGEN; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT;

ADDITION REACTION; ARYLATION; CARBOMAGNESATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; GRIGNARD REACTION; METHYLATION; REVIEW; STOICHIOMETRY;

EID: 0345921708     PISSN: 15711013     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1023432624548     Document Type: Review

References (31)

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14. 4] have been reported: R.J. Morris and G.S. Girolami, Organometallics 8 (1989) 1478. The reaction of tetrafurylmanganate has been reported: G. Cahiez, P.-Y. Chavant and E. Metais, Tetrahedron Lett. 33 (1992) 5245.
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16. 4] have been reported: R.J. Morris and G.S. Girolami, Organometallics 8 (1989) 1478. The reaction of tetrafurylmanganate has been reported: G. Cahiez, P.-Y. Chavant and E. Metais, Tetrahedron Lett. 33 (1992) 5245.
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18. For examples of phenylalumination of acetylenes, see J.J. Eisch and W.C. Kaska, J. Am. Chem. Soc. 88 (1966) 2976; J.J. Eisch, R. Amtmann and M.W. Foxton, J. Organomet. Chem. 16 (1969) P55; J.J. Eisch and R. Amtmann, J. Org. Chem. 37 (1972) 3410. 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 (1997) 93.
19. For examples of phenylalumination of acetylenes, see J.J. Eisch and W.C. Kaska, J. Am. Chem. Soc. 88 (1966) 2976; J.J. Eisch, R. Amtmann and M.W. Foxton, J. Organomet. Chem. 16 (1969) P55; J.J. Eisch and R. Amtmann, J. Org. Chem. 37 (1972) 3410. 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 (1997) 93.
20. For examples of phenylalumination of acetylenes, see J.J. Eisch and W.C. Kaska, J. Am. Chem. Soc. 88 (1966) 2976; J.J. Eisch, R. Amtmann and M.W. Foxton, J. Organomet. Chem. 16 (1969) P55; J.J. Eisch and R. Amtmann, J. Org. Chem. 37 (1972) 3410. 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 (1997) 93.
21. For examples of phenylalumination of acetylenes, see J.J. Eisch and W.C. Kaska, J. Am. Chem. Soc. 88 (1966) 2976; J.J. Eisch, R. Amtmann and M.W. Foxton, J. Organomet. Chem. 16 (1969) P55; J.J. Eisch and R. Amtmann, J. Org. Chem. 37 (1972) 3410. 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 (1997) 93.
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27. For silylmetalation of alkynes, see H. Hayami, M. Sato, S. Kanemoto, Y. Morizawa, K. Oshima and H. Nozaki, J. Am. Chem. Soc. 105 (1983) 4491; K. Nozaki, K. Wakamatsu, T. Nonaka, W. Tückmantel, K. Oshima and K. Utimoto, Tetrahedron Lett. 27 (1986) 2007; K. Wakamatsu, T. Nonaka, Y. Okuda, W. Tückmantel, K. Oshima, K. Utimoto and H. Nozaki, Tetrahedron 42 (1986) 4427; I. Fleming, T.W. Newton and F. Roessler, J. Chem. Soc. Perkin Trans. I (1981) 2527; K. Tamao, M. Akita, R. Kanatani, N. Ishida and M. Kumada, J. Organomet. Chem. 226 (1982) C9.
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31. Recently, we have reported selective formation of six-membered bicyclic compounds with chromium reagents: T. Nishikawa, H. Kakiya, H. Shinokubo and K. Oshima, J. Am. Chem. Soc. 123 (2001) 4629.