New method for the preparation of an active manganese species and its use for radical cyclization reactions

Synlett

Volumn , Issue 10, 1998, Pages 1075-1076

  Tang, Jun ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002912915     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1897     Document Type: Article

References (12)

1. Inoue, R.; Nakao, J.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn., 1997, 70, 2039.
2. Metal granules 1-3 mm; Purchased from Mitsuwa's pure chemicals.
3. The blank test without manganese species was performed as follows. The supernatant liquid containing magnesium species in THF (5 mL) was added to the flask containing Id (X=I) (1.0 mmol) in THF (2 mL). No reaction was observed after 24 h from which 90% of the starting material was recovered unchanged.
4. Cahiez, G.; Alami, M. Tetrahedron, 1989, 45, 4163.
5. 4: Hiyama, T.; Obayashi, M.; Nakamura, A. Organometallics, 1982, 1, 1249;
6. Li-naphthalene: Kim, S.-H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett., 1996, 37, 2197;
7. 8K: Fürstner, A.; Brunner, H. Tetrahedron Lett., 1996, 37, 7009.
8. Treatment of 1b (X=I) with commercially available manganese powder (Kanto Chemical Co. Inc) at 25 °C for 36 h resulted in a complete recovery of the starting material. Several procedures for activation of Mn metal have been reported: Hiyama, T.; Sawahata, M.; Obayashi, M. Chem. Lett., 1983, 1237;
9. Cahiez, G.; Chavant, P. Y. Tetrahedron Lett., 1989, 30, 7373;
10. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett., 1996, 37, 7049.
11. -1). Newcomb, M.; Curran, D. P. Acc. Chem. Res., 1988, 21, 206.
12. Three-component coupling reactions of alkyl iodides, electronic deficient olefins, and carbonyl compounds with manganese-lead reducing reagent have been reported. Takai, K.; Ueda, T.; Ikeda, N.; Moriwake, T. J. Org. Chem., 1996, 61, 7990.