Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5785-5788

  Chakraborti, Asit K ^a   Shivani, ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDRIDES; CHEMOSELECTIVE ACETYLATION; ELECTROPHILIC ANHYDRIDES; STERIC FACTORS;

ACYLATION; CATALYSTS; ELECTRONS; REACTION KINETICS; SOLVENTS;

MAGNESIUM COMPOUNDS;

ACID ANHYDRIDE; ALCOHOL; BENZOIC ACID DERIVATIVE; CHLOROACETIC ACID; ISOBUTYRIC ACID DERIVATIVE; MAGNESIUM BISTRIFLUOROMETHANESULFONIMIDE; MAGNESIUM DERIVATIVE; PHENOL DERIVATIVE; PIVALIC ACID; PROPIONIC ACID DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

ACETYLATION; ACYLATION; ALCOHOLS; ANHYDRIDES; CATALYSIS; CYCLIZATION; IMIDES; MAGNESIUM; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PENTANOIC ACIDS; SULFONIUM COMPOUNDS;

EID: 33746335364     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0605142     Document Type: Article

References (44)

1. Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999.
2. (a) Nafion-H: Kumareswaran, R.; Pachamuthu, K.; Vankar, Y. D. Synlett 2000, 1651-1654.
3. (b) Yttria-zirconia: Kumar, P.; Pandey, R. K.; Bodas, M. S.; Dongare, M. K. Synlett 2001, 206-209.
4. (c) NBS: Karimi, B.; Seradj, H. Synlett 2001, 519-520.
5. 4: Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 1581-1586.
6. (e) Ionic liquid: Forsyth, S. A.; MacFarlane, D. R.; Thompson, R. J.; Itzstein, M. V. Chem. Commun. 2002, 714-715.
7. 2: Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Synlett 2003, 39-42.
8. 2: Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Sambri, L. Eur. J. Org. Chem. 2003, 4611-4617.
9. 40: Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K. Chem. Commun. 2003, 764-765.
10. 3: De, S. K. Tetrahedron Lett. 2004, 45, 2919-2922.
11. 2: Ghosh, R.; Maiti, S.; Chakraborty, A. Tetrahedron Lett. 2004, 45, 147-151.
12. (k) BiOCl: Ghosh, R.; Maiti, S.; Chakraborty, A. Tetrahedron Lett. 2004, 45, 6775-6778.
13. 3: Yadav, V. K.; Babu, K. G. J. Org. Chem. 2004, 69, 577-580.
14. 2: Chen, C.-T.; Kuo, J.-H.; Pawar, V. D.; Munot, Y. S.; Weng, S.-S.; Ku, C-H.; Liu, C.-Y. J. Org. Chem. 2005, 70, 1188-1197.
15. 2Cl: Salavati-Niasari, M.; Hydrazadeh, S.; Amiri, A.; Salavati, S. J. Mol. Catal. A 2005, 231, 191-195.
16. 2: Chandra, K. L.; Saravanan, P.; Singh, R. K.; Singh, V. K. Tetrahedron 2002, 58, 1369-1374.
17. 3: Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett 1999, 1743-1744.
18. 3: Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. J. Org. Chem. 2001, 66, 8926-8934.
19. 3: Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio, A.; Nardi, M.; Bartoli, G.; Romeo, R. Tetrahedron Lett. 2003, 44, 5621-5624.
20. (e) LiOTf: Karimi, B.; Maleki, J. J. Org. Chem. 2003, 68, 4951-4954.
21. 3: Procopio, A.: Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Russo, B.; Sindona, G. Adv. Synth. Catal. 2005, 346, 1465-1470.
22. 2: Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896-1897.
23. 4: Chakraborti, A. K.; Gulhane, R.; Shivani. Synlett 2003, 1805-1808.
24. 2: Chakraborti, A. K.; Sharma, L.; Gulhane, R.; Shivani. Tetrahedron 2003, 59, 7661-7668.
25. 2: Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 3521-3525.
26. 2: Chakraborti, A. K.; Gulhane, R.; Shivani. Synthesis 2004, 111-115.
27. 3: Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 6749-6753.
28. 4: Chakraborti, A. K.; Gulhane, R. Synlett 2004, 627-630.
29. Olah, G. A.; Prakash, G. K. S. Superacids; Wiley: New York, 1985.
30. Dumeunier, R.; Markó, I. E. Tetrahedron Lett. 2004, 45, 825-882.
31. (a) Schumacher, J. C. Perchlorates; Their Properties, Manufacture and Uses; ACS Monograph Series; Reinhold: New York, 1960.
32. (b) Long, J. Chem. Health Saf. 2002, 9, 12-18.
33. Foropoulos, J.; DesMarteau, D. D. Inorg. Chem. 1984, 23, 3720-3123.
34. Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565.
35. (a) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 55, 8219-8226.
36. (b) Vij, A.; Zheng, Y. Y.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem. 1994, 33, 3281-3288.
37. (c) Olah, G. A.; Laali, K.; Farooq, O. Organometallics 1984, 3, 1337-1340.
38. (a) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565-567.
39. (b) Ghosez, L.; Mineur, C.; Tamion, R. Tetrahedron Lett. 1995, 36, 8977-8980.
40. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266.
41. Huheey, J. E. Inorganic Chemistry: Principles of Structure and Reactivity, 3rd ed.; Harper & Row: Singapore, 1983.
42. (a) Yatsimirksii, K. B.; Vasil'ev, V. P. Instability Constants of Complex Compounds; Pergamon: Elmsford, NY, 1960.
43. (b) Bjerrum, B., Schwarzenbach, G., Sillen, L. G., Eds. Stability Constants of Metal-Ion Complexes, Part II: Inorganic Ligands; The Chemical Society: London, 1958.
44. Sibi, M. P.; Petrovic, G. Tetrahedron: Asymmetry 2003, 14, 2879-2882 and references therein.