PMA-SiO2: A heterogenous catalyst for O-, S-, and N-nucleophilic substitution reactions of aryl propargyl alcohols

Synthetic Communications

Volumn 38, Issue 9, 2008, Pages 1448-1455

  Srihari, P ^a   Reddy, J Shyam Sunder ^a   Bhunia, Dinesh C ^a   Mandal, S S ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Allylation; Heteropolyacid; Nicholas reaction; Propargyl alcohol; Propargylation

Indexed keywords

ALCOHOL; PHOSPHOMOLYBDIC ACID; SILICA GEL; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 42149165528     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801914335     Document Type: Article

References (42)

1. (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I. (Ed.); Wiley-VCH: New York, 2000, chapter 8E;
2. (b) Matsuda, S.; Momori, K.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 9072;
3. (c) Elsevier, C. J.; Kieijin, H.; Boersma, J.; Vermeer, P. Organometallics 1986, 5, 716;
4. (d) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
5. (a) Nicholas, K. M.; Mulvaney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508;
6. (b) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 27;
7. (c) Montana, A. M.; Fernandez, D. Tetrahedron Lett. 1999, 40, 6499;
8. (d) Kuhn, O.; Rau, D.; Mayr, H. J. Am. Chem. Soc. 1998, 120, 900;
9. (e) B. K. Ph.D. Dissertation, Cornell University, 1995;
10. (f) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., and Wilkinson, J. (Eds.); Pergamon Press: Oxford 1995; Vol. 12, chapter 7.1, p. 685;
11. (g) Green, J. R. Curr. Org. Chem. 2001, 5, 809.
12. For various applications of the Nicholas reactions, see (h) Qunital, M. M.; Colsser, K. D.; Shea, K. V. Org. Lett. 2004, 6, 4949;
13. (i) Berge; Claridge, S.; Mann, A.; Muller, C.; Tyrrell, E. Tetrahedron Lett. 1997, 38, 685.
14. (a) Ohri, R. V.; Radosevich, A. T.; Hrovat, K. J.; Musich, C.; Huang, D.; Holman, T. R.; Toste, F. D. Org. Lett. 2005, 7, 2501;
15. (b) Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 15760.
16. (a) Nishibayashi, Y.; Wakiji, I.; Ishii, Y.; Uemura, S.; Hidai, M. J. Am. Chem. Soc. 2001, 123, 3393;
17. (b) Nishibayashi, Y.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2003, 22, 873;
18. (c) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Org. Chem. 2004, 69, 3408.
19. Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 14180;
20. (b) Liu, J. H.; Muth, E.; Florke, U.; Henkel, G.; Merz, K.; Sauvageau, J.; Schwake, E.; Dyker, G. Adv. Synth. Catal. 2006, 348, 456.
21. (a) Mahrwald, R.; Quint, S. Tetrahedron Lett. 2001, 42, 1655;
22. (b) Imada, Y.; Yuasa, M.; Nakamura, I.; Murahashi, S. I. J. Org. Chem. 1994, 59, 2282;
23. (c) Schwier, T.; Rubin, M.; Gevorgyan, V. Org. Lett. 2004, 6, 1999;
24. (d) Mahrwald, R.; Quint, S.; Scholtis, S. Tetrahedron 2002, 58, 9847;
25. (e) Bartels, A.; Mahrwald, R.; Qunit, S. Tetrahedron Lett. 1999, 40, 5989;
26. (f ) Kondo, T.; Kanda, Y.; Baba, A.; Fukuda, K.; Nakamura, A.; Wada, K.; Morisaki, Y.; Mitsudo, T. A. J. Am. Chem. Soc. 2002, 124, 12960.
27. Yoshimatsu, M.; Shimizu, H.; Kataoka, T. Chem. Commun. 1995, 149.
28. (a) Zhan, Z-P.; Yu, J.-L.; Liu, H.-J.; Cui, Y.-Y.; Yang, R.-F.; Yang, W.-Z.; Li, J.-P. J. Org. Chem. 2006, 71, 8298;
29. (b) Zhan, Z. P.; Yang, W. Z.; Yang, R. F.; Yu, J. L.; Li, J. P.; Liu, H. J. Chem. Commun. 2006, 3352.
30. (a) Anastas, P. T.; Williamson, T. C. Green Chemistry: Designing for the Environment; Anastas, P. T., Williamson, T. C. (Eds.); American Chemical Society: Washington, DC, 1996, pp. 1-17;
31. (b) Anastas, P. T.; Kirchhoff, M. M.; Williamson, T. C. Appl. Catal., A 2001, 221, 3.
32. (a) Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171;
33. (b) Mizuno, N.; Misono, M. Chem. Rev. 1998, 98, 199;
34. (c) Misono, M.; Ono, I.; Koyano, G.; Aoshima, A. Pure Appl. Chem. 2000, 72, 1305;
35. (d) Wilson, K.; Clark, J. H. Pure Appl. Chem. 2000, 72, 1313;
36. (e) Bamoharram, F. F.; Heravi, M. M.; Roshani, M.; Gharib, A.; Jahangir, M. J. Mol. Catal. A.: Chem. 2006, 252, 90.
37. Crisostomo, F. R. P.; Carrillo, R.; Martin, T.; Martin, V. S. Tetrahedron Lett. 2005, 46, 2829.
38. (a) Yadav, J. S.; Satyanarayana, M.; Balanarsaiah, E.; Raghavendra, S. Tetrahedron Lett. 2006, 47, 6095;
39. (b) Yadav, J. S.; Raghavendra, S.; Satyanarayana, M.; Balanarsaiah, E. Synlett 2005, 16, 2461.
40. 2 from other groups, see; (c) Kishore Kumar, G. D.; Baskaran, S. J. Org. Chem. 2005, 70, 4520;
41. (d) Kishore Kumar, G. D.; Baskaran, S. Chem. Commun. 2004, 1026;
42. (e) Kishore Kumar, G. D.; Baskaran, S. Synlett 2004, 1719.