Halogen-magnesium exchange via trialkylmagnesates for the preparation of aryl- and alkenymagnesium reagents

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2481-2483

  Kitagawa, Kazuya ^a   Inoue, Atsushi ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Ate complexes; Grignard reactions; Magnesium; Metalations

Indexed keywords

ALKYL GROUP; HALOGEN; MAGNESIUM; MAGNESIUM DERIVATIVE; REAGENT;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; TEMPERATURE DEPENDENCE;

EID: 0034679511     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2481::AID-ANIE2481>3.0.CO;2-J     Document Type: Article

References (27)

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18. For further examples of halogen-magnesium exchange reactions, see; a) N. Furukawa, T. Shibutani, H. Fujihara, Tetrahedron Lett. 1987, 28, 5845-5848; b) H. Nishikawa, K. Isaka, K. Itoh, K. Ohno, H. Nagase, K. Matsumoto, H. Yoshiwara, J. Org. Chem. 1992, 57, 407-410; c) H. Shinokubo, H. Miki, T. Yokoo, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 11 681-11 692; d) F. Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron Lett. 1999, 40, 4339-4342.
19. For further examples of halogen-magnesium exchange reactions, see; a) N. Furukawa, T. Shibutani, H. Fujihara, Tetrahedron Lett. 1987, 28, 5845-5848; b) H. Nishikawa, K. Isaka, K. Itoh, K. Ohno, H. Nagase, K. Matsumoto, H. Yoshiwara, J. Org. Chem. 1992, 57, 407-410; c) H. Shinokubo, H. Miki, T. Yokoo, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 11 681-11 692; d) F. Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron Lett. 1999, 40, 4339-4342.
20. For further examples of halogen-magnesium exchange reactions, see; a) N. Furukawa, T. Shibutani, H. Fujihara, Tetrahedron Lett. 1987, 28, 5845-5848; b) H. Nishikawa, K. Isaka, K. Itoh, K. Ohno, H. Nagase, K. Matsumoto, H. Yoshiwara, J. Org. Chem. 1992, 57, 407-410; c) H. Shinokubo, H. Miki, T. Yokoo, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 11 681-11 692; d) F. Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron Lett. 1999, 40, 4339-4342.
21. For further examples of halogen-magnesium exchange reactions, see; a) N. Furukawa, T. Shibutani, H. Fujihara, Tetrahedron Lett. 1987, 28, 5845-5848; b) H. Nishikawa, K. Isaka, K. Itoh, K. Ohno, H. Nagase, K. Matsumoto, H. Yoshiwara, J. Org. Chem. 1992, 57, 407-410; c) H. Shinokubo, H. Miki, T. Yokoo, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 11 681-11 692; d) F. Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron Lett. 1999, 40, 4339-4342.
22. 2 has been reported: L. M. Seitz, T. L. Brown, J. Am. Chem. Soc. 1966, 88, 4140- 4147.
23. 2 has been reported: L. M. Seitz, T. L. Brown, J. Am. Chem. Soc. 1966, 88, 4140- 4147.
24. 2 has been reported: L. M. Seitz, T. L. Brown, J. Am. Chem. Soc. 1966, 88, 4140-4147.
25. 3MgLi provided the corresponding product in 85% yield upon treatment with propanal.
26. 2MgLi, whereas bromobenzene did not react iPrMgBr at ⋯ 78 C.
27. 2MgLi, provided no isopropyl-substituted alcohol. The isopropyl group was consumed for the exchange reaction. This result indicates that the isopropyl residue in the mixed ate complex is active.