Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines

Tetrahedron Letters

Volumn 45, Issue 14, 2004, Pages 2919-2922

  Kanta De, Surya ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; ALCOHOL DERIVATIVE; AMINE; CHLORINE DERIVATIVE; LEWIS ACID; PHENOL DERIVATIVE; RUTHENIUM COMPLEX; SOLVENT; THIOL DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SOLVENT EFFECT;

EID: 1642274391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.071     Document Type: Article

References (20)

1. Greene T.W., Wuts P.G.M. Protective groups in Organic Synthesis. 3rd ed. 1999;Wiley, New York. p 150.
2. Vedejs E., Diver S.T. J. Am. Chem. Soc. 115:1993;3358.
3. Ishihara K., Kubota M., Kurihara H., Yamamoto H. J. Am. Chem. Soc. 117:1995;4413.
4. Ishihara K., Kubota M., Kurihara H., Yamamoto H. J. Org. Chem. 61:1996;4560.
5. Ishihara K., Kubota M., Yamamoto H. Synlett. 1996;265.
6. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A. J. Org. Chem. 63:1998;2342.
7. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A. Chem. Commun. 1996;2625.
8. Saravanan P., Singh V.K. Tetrahedron Lett. 40:1999;2611.
9. Chandra K.L., Saravanan P., Singh R.K., Sing V.K. Tetrahedron. 58:2002;1369.
10. Chakroborty A., Gulhane R. Tetrahedron Lett. 44:2003;6749.
11. Chauhan K.K., Frost C.G., Love I., Waite D. Synlett. 1999;1743.
12. Orita A., Tanahashi C., Kakuda A., Otera J. Angew. Chem., Int. Ed. 39:2000;2877.
13. Orita A., Tanahashi C., Kakuda A., Otera J. J. Org. Chem. 66:2001;8926.
14. Carrigan M.D., Freiberg D.A., Smith R.C., Zerth H.M., Mohan R.S. Synthesis. 2001;2091.
15. Chandrasekhar S., Ramchander T., Takhi M. Tetrahedron Lett. 39:1998;3263.
16. Ballini R., Bosica G., Carloni S., Ciaralli L., Maggi R., Sartori G. Tetrahedron Lett. 39:1998;6049.
17. Bhaskar P.M., Loganathan D. Tetrahedron Lett. 39:1998;2215.
18. Li A.-X., Li T.-S., Ding T.-H. Chem. Commun. 1997;1389.
19. Nakae Y., Kusaki I., Sato T. Synlett. 2001;1584.
20. 3): δ 1.35-1.48 (m, 4H), 1.64 (quintet, J=7 Hz, 2H), 1.87 (quintet, J=6.8 Hz, 2H), 2.01 (s, 3H), 3.41 (t, J=7 Hz, 2H), and 4.06 (t, J=7 Hz, 2H). The commercially available anhydrous ruthenium chloride (Aldrich) was used in all reactions. I have also observed that ruthenium chloride trihydrate can be used for the acetylation reaction but requires more catalyst and longer reaction times than anhydrous ruthenium chloride.