Magnesiation of functionalized iodobenzenes at room temperature: Clarification of the stability of ethoxycarbonylphenylmagnesium iodides

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1915-1917

  Sugimoto, Osamu ^a   Aoki, Keiji ^a   Tanji, Ken Ichi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Active magnesium; Grignard reagent; Magnesiation

Indexed keywords

AROMATIC COMPOUND; CARBONYL DERIVATIVE; ETHYL 3 IODOBENZOATE; ETHYL 4 IODOBENZOATE; HALIDE; IODOBENZENE; MAGNESIUM; MAGNESIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; DECOMPOSITION; MAGNESIATION; REACTION ANALYSIS; REACTION TIME; ROOM TEMPERATURE;

EID: 1242293810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.136     Document Type: Article

References (12)

1. Sapountzis I., Knochel P. J. Am. Chem. Soc. 124:2002;9390-9391.
2. Jensen A.E., Dohle W., Sapountzis I., Lindsay D.M., Vu V.A., Knochel P. Synthesis. 2002;565-569.
3. Dohle W., Lindsay D.M., Knochel P. Org. Lett. 3:2001;2871-2873.
4. Abarbri M., Thibonnet J., Berillon L., Dehmel F., Rottlander M., Knochel P. J. Org. Chem. 65:2000;4618-4634.
5. Boymond L., Rottlander M., Cahiez G., Knochel P. Angew. Chem., Int. Ed. 37:1998;1701-1703.
6. Kitagawa K., Inoue A., Shinokubo H., Oshima K. Angew. Chem., Int. Ed. 39:2000;2481-2483.
7. Inoue A., Kitagawa K., Shinokubo H., Oshima K. J. Org. Chem. 66:2001;4333-4339.
8. Lee J., Velarde-Ortiz R., Guijarro A., Wurst J.R., Rieke R.D. J. Org. Chem. 65:2000;5428-5430.
9. General procedure: To a suspension of Mg* (6.00 mmol) in tetrahydrofuran (30 mL), the substrate (2.4 mmol) was added at -70°C and the mixture was stirred for an appropriate time. The reaction mixture was quenched with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and treated with silica gel chromatography to give ethyl benzoate.
10. Preparation of Mg*: Under argon atmosphere, a mixture of lithium wire (ALDRICH, Catalog No. 27,832-7; 83.3 mg, 12.0 mmol), naphthalene (1538 mg, 12.0 mmol), magnesium chloride powder (ALDRICH, Catalog No. 24,413-9; 571 mg, 6.00 mmol), and tetrahydrofuran (30 mL) was stirred at room temperature until lithium was completely consumed (2-3 h) to give a gray suspension of Mg* (about 0.2 M). The amount of these reagents may be used in proportion to that of the substrate.
11. 3: C, 71.16; H, 8.53. Found: C, 71.18; H, 8.48.
12. Sugimoto O., Yamada S., Tanji K. J. Org. Chem. 68:2003;2054-2057.