Organocatalytic methods for chemoselective O-tert-butoxycarbonylation of phenols and their regeneration from the O-t-Boc derivatives

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8615-8618

  Chankeshwara, Sunay V ^a   Chebolu, Rajesh ^a   Chakraborti, Asit K ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; BITS; CARBON DIOXIDE; CARBONATES; CHEMICAL BONDS; CHEMICAL REACTIONS; ESTERIFICATION; ESTERS; ETHERS; ORGANIC COMPOUNDS;

ALKYL ESTERS; ALKYL ETHERS; BUTOXYCARBONYLATION; CARBON TETRABROMIDE; CATALYST SYSTEMS; CHEMICAL EQUATIONS; CHEMOSELECTIVE; CYCLIC CARBONATES; DOUBLE BONDS; FUNCTIONALIZED; NITRENE; PROTECTING GROUPS; SIDE REACTIONS;

PHENOLS;

ACETAL DERIVATIVE; ALKENE DERIVATIVE; ALKYL ETHER; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; ORGANIC COMPOUND; PHENOL DERIVATIVE;

ARTICLE; BROMINATION; CARBONYLATION; CATALYSIS; CATALYST; REACTION ANALYSIS; TRANSESTERIFICATION;

CATALYSIS; ESTERIFICATION; FORMIC ACID ESTERS; METHODS; PHENOLS;

EID: 55249124274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8013325     Document Type: Article

References (46)

1. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
2. Greene, T. W.; Wuts, P. G. M. Protective Groups Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
3. (a) Shivani; Gulhane, R.; Chakraborti, A. K. J. Mol. Catal. A: Chem. 2007, 264, 208.
4. (b) Chakraborti, A. K.; Shivani, J. Org. Chem. 2006, 71, 5785.
5. (c) Chakraborti, A. K.; Gulhane, R. Synlett 2004, 627.
6. (d) Chakraborti, A. K.; Gulhane, R. Synthesis 2004, 111.
7. (e) Chakraborti, A. K.; Gulhane, R.; Shivani, Synlett 2003, 1805.
8. (f) Chakraborti, A. K.; Sharma, L.; Gulhane, R.; Shivani, Tetrahedron 2003, 59, 7661.
9. (g) Chakraborti, A. K.; Gulhane, R. J. Chem. Soc., Chem. Commun. 2003, 1896.
10. (h) Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 3521.
11. (a) Chakraborti, A. K.; Sharma, L.; Nayak, M. K. J. Org. Chem. 2002, 67, 2541.
12. (b) Chakraborti, A. K.; Nayak, M. K.; Sharma, L. J. Org. Chem. 1999, 64, 8027.
13. (a) Houlihan, F.; Bouchard, F.; Fréchet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153.
14. (b) Hansen, M.; Riggs, J. R. Tetrahedron Lett. 1998, 39, 2705.
15. (c) Basel, Y.; Hassner, A. J. Org. Chem. 2000, 65, 6368.
16. (d) Ouchi, H.; Saito, Y.; Yamamoto, Y.; Takahata, H. Org. Lett. 2002, 4, 585.
17. (e) Saito, Y.; Ouchi, H.; Takahata, H. Tetrahedron 2006, 62, 11599.
18. (f) Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Locatelli, M.; Melchiorre, P.; Palazzi, P.; Sambri, L. Synlett 2006, 2104.
19. (a) Chankeshwara, S. V.; Chakraborti, A. K. Synthesis 2006, 2784.
20. (b) Chakraborti, A. K.; Chankeshwara, S. V. Org. Biomol. Chem. 2006, 4, 2769.
21. (c) Chankeshwara, S. V.; Chakraborti, J. Mol. Catal. A: Chem. 2006, 253, 198.
22. (d) Chankeshwara, S. V.; Chakraborti, Tetrahedron Lett. 2006, 47, 1087.
23. Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Locatelli, M.; Marcantoni, E.; Melchiorre, P.; Sambri, L. J. Org. Chem. 2006, 71, 9580.
24. Chebolu, R.; Chankeshwara, S. V.; Chakraborti, A. K. Synthesis 2008, 1448.
25. Woiwode, T. F.; Rose, C.; Wandless, T. J. J. Org. Chem. 1998, 63, 9594.
26. (a) Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jenings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green Chem. 2008, 10, 31.
27. (b) Capello, C.; Fischer, U.; Hungerbühler, K. Green Chem. 2007, 9, 927.
28. Hunter, W. H.; Edgar, D. E. J. Am. Chem. Soc. 1932, 54, 2025.
29. Burk, M. J.; Allen, J. G. J. Org. Chem. 1997, 62, 7054.
30. Kharasch, M. S.; Jensen, E. V.; Urry, W. H. J. Am. Chem. Soc. 1946, 68, 154.
31. (a) Lee, A. S.-Y.; Yeh, H.-C.; Shie, J.-J. Tetrahedron Lett. 1998, 39, 5249.
32. (b) Chen, M.-Y.; Lee, A. S.-Y. J. Org. Chem. 2002, 67, 1384.
33. 4 has been used as organocatalyst, but its role has not been defined except for the proposition of its mild Lewis acid property. Zhang, L.; Luo, Y.; Fan, R.; Wu, J. Green Chem. 2007, 9, 1022, and references therein.
34. Stevenson, D. P.; Coppinger, G. M. J. Am. Chem. Soc. 1962, 84, 149.
35. Janini, G. M.; King, J. W.; Martire, D. E. J. Am. Chem. Soc. 1974, 96, 5268.
36. (a) Lindeman, S. V.; Hecht, J.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 11597.
37. (b) Shen, J.; Cheng, W.-D.; Wu, D.-S.; Lan, Y.-Z.; Li, F.-F.; Huang, S.-P.; Zhang, H.; Gong, Y.-J. J. Phys. Chem. A 2006, 110, 10330.
38. Orvik, J. A. J. Org. Chem. 1996, 61, 4933.
39. Nakamura, K.; Nakajima, T.; Kayahara, H.; Nomura, E.; Taniguchi, H. Tetrahedron Lett. 2004, 45, 495.
40. (a) Lee, J. B.; Nolan, T. J. Can. J. Chem. 1966, 44, 1331.
41. (b) Kocienski, P. J.; Cernigliaro, G.; Feldstein, G. J. Org. Chem. 1977, 42, 353.
42. Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
43. (a) Cadogan, J. I. G.; Cameron-Wood, M.; Mackie, R. K.; Searle, R. J. G. J. Chem. Soc. 1965, 4831.
44. (b) Freeman, A. W.; Urvoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014.
45. Hagiwara, H.; Morohashi, K.; Sakai, H.; Suzuki, T.; Ando, M. Tetrahedron 1998, 54, 5845.
46. Johnstone, C.; Kerr, W. J.; Scott, J. S. Chem. Commun. 1996, 341.