Design of ionic liquids as a medium for the Grignard reaction

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7774-7777

  Itoh, Toshiyuki ^a   Kude, Keisuke ^a   Hayase, Shuichi ^a   Kawatsura, Motoi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ETHER; FLUORINE DERIVATIVE; GRIGNARD REAGENT; IMIDE; IONIC LIQUID; METHANE; PHOSPHONIUM DERIVATIVE; REAGENT; SOLVENT; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; GRIGNARD REACTION; HYDROPHOBICITY; MOLECULAR STABILITY; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 34848924293     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.010     Document Type: Article

References (21)

1. For recent reviews of reactions in an ionic liquid solvent system see:. In: Wasserscheid P., and Welton T. (Eds). Ionic Liquids in Synthesis (2003), Wiley-VCH
2. In: Rogers R.D., and Seddon K.R. (Eds). Ionic Liquids as Green Solvents. ACS Symposium Series Vol. 856 (2002), American Chemical Society
3. Jain N., Kumar A., Chauhan S., and Chauhan S.M.S. Tetrahedron 61 (2005) 1015-1060
4. Chowdhury S., Mohan R.S., and Scott J.L. Tetrahedron 63 (2007) 2363-2389
5. Recent examples see:. Ohara H., Kiyokane H., and Itoh T. Tetrahedron Lett. 43 (2002) 3041-3044
6. Itoh T., Kawai K., Hayase S., and Ohara H. Tetrahedron Lett. 44 (2003) 4081-4084
7. Uehara H., Nomura S., Hayase S., Kawatsura M., and Itoh T. Electrochemistry 74 (2006) 635-638
8. Tsukada Y., Iwamoto K., Furutani H., Matsushita Y., Abe Y., Matsumoto K., Monda K., Hayase S., Kawatsura M., and Itoh T. Tetrahedron Lett. 48 (2006) 1801-1804
9. Itoh T., Matsushita Y., Abe Y., Han S.-H., Wada S., Hayase S., Kawatsura M., Takai S., Morimoto M., and Hirose Y. Chem. Eur. J. 12 (2006) 9228-9237
10. Ramnial T., Ino D.D., and Clyburne J.A.C. Chem. Commun. (2005) 325
11. Jurcik V., and Wilhelm R. Green Chem. 7 (2005) 844-848
12. Handy S.T. J. Org. Chem. 71 (2006) 4659-4662
13. Law M.C., Wong K.-Y., and Chan T.H. Chem. Commun. (2006) 2457-2459
14. For this ionic liquid, please contact Dr. Gen Masuda of Nissinbo Co., Ltd Tel.: +81 43 205 0795, fax: +81 43 205 0842.
15. Ramnial T., Taylor S.A., Clybume J.A.C., and Walsby C.J. Chem. Commun. (2007) 2066-2068
16. Itoh, T.; Kude, K.; Iwai, A.; Hayase, S.; Kawatsura, M. Abstract of 86th CSJ Annual Meeting, 1D3-39, Osaka, March 25, 2007.
17. Wakefield B.J. In: Barton D.H.R., and Ollis W.D. (Eds). Comprehensive Organic Chemistry Vol. 3 (1979) Chapter 15.2
18. A recent good example, see:. Zhou Z.-B., Matsumoto H., and Tatsumi K. Chem. Eur. J. 11 (2005) 752-766 and references cited therein
19. -1. Since ionic liquids, IL1b, IL1d, IL2a, IL2b, and IL2d, showed poor properties as reaction media, we did not attempt further purification.
20. Since IL1a does exhibit slight solubility in ether, over the course of extraction workup, the volume of the IL remaining will decrease. Fortunately, the use of 25% ether in hexane solution was sufficient to extract the products from the IL.
21. For this novel ionic liquid, please contact Dr. Katsuhiko Tsunashima of Nippon Kagaku Industry Co., Ltd Tel.: +81 3 3636 8090; fax: +81 3 3636 8071. E-mail: katsuhiko.tsunashima@nippon-chem.co.jp.