The new synthesis and characterization of SBA-15-Pr–NMe3OH: a tailored and reusable Bronsted base nanoreactor for the conversion of nitriles into amides using H2O2
Source abstract
Abstract
A novel method for the synthesis of SBA-15-Pr–NMe3OH as a nanoreactor heterogenous Bronsted base catalyst has been developed. Quaternary organic tetraalkylammonium hydroxide grafted on SBA-15 is a strong Bronsted base catalyst, and represents a useful alternative to soluble bases in the selective conversion of nitriles to amides with aqueous 30 % H2O2, presenting high efficiency, convenient recovery and steady reuse.
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Research context
OpenAlex topics: Chemical Synthesis and Analysis · Chemical Synthesis and Reactions · Asymmetric Hydrogenation and Catalysis
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References (53)
Show source-provided references
1. F. Hoffmann, M. Cornelius, J. Morell, M. Fröba, Angew. Chem. Int. Ed. 45, 3216 (2006)10.1002/anie.200503075 ↗
2. X. Pan, Z. Fan, W. Chen, Y. Ding, H. Luo, X. Bao, Nat. Mater. 6, 507 (2007)10.1038/nmat1916 ↗
3. E. Castillejos, P.-J. Debouttiere, L. Roiban, A. Solhy, V. Martinez, Y. Kihn, O. Ersen, K. Philippot, B. Chaudret, P. Serp, Angew. Chem. Int. Ed. 48, 2529 (2009)10.1002/anie.200805273 ↗
4. P. Serp, E. Castillejos, Chem. Cat. Chem. 2, 41 (2010)
5. T. Mitsudome, K. Nose, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, Angew. Chem. Int. Ed. 46, 3288 (2007)10.1002/anie.200604644 ↗
6. S. Mandal, D. Roy, R.V. Chaudhari, M. Sastry, Chem. Mater. 16, 3714 (2004)10.1021/cm0352504 ↗
7. R. Zhang, W. Ding, B. Tu, D. Zhao, Chem. Mater. 19, 4379 (2007)10.1021/cm071718h ↗
8. Q. Yang, D. Han, H. Yang, C. Li, Chem. Asian J. 3, 1214 (2008)10.1002/asia.200800110 ↗
9. K. Qian, J. Wan, F. Liu, H.H. Girault, B. Liu, C. Yu, ACS Nano 3, 3656 (2009)10.1021/nn900739z ↗
10. Z.J. Chen, Z.H. Guan, M.R. Li, Q.H. Yang, C. Li, Angew. Chem. Int. Ed. 50, 4913 (2011)10.1002/anie.201006870 ↗
11. H.-S. Xia, C.-H. Zhou, D.S. Tong, C.X. Lin, J. Porous Mater. 17, 225 (2010)10.1007/s10934-009-9284-5 ↗
12. Q. Yang, J. Liu, L. Zhang, C. Li, J. Mater. Chem. 19, 1945 (2009)10.1039/b815012e ↗
13. S.L. Burkett, S.D. Sims, S. Mann, Chem. Commun. 1367 (1996)10.1039/CC9960001367 ↗
14. D.J. Macquarrie, Chem. Commun. 1961 (1996)10.1039/CC9960001961 ↗
15. N. Mizoshita, T. Tani, S. Inagaki, Chem. Soc. Rev. 40, 789 (2011)10.1039/C0CS00010H ↗
16. T. Asefa, M.J. MacLachlan, N. Coombs, G.A. Ozin, Nature 402, 867 (1999)10.1038/47229 ↗
17. J.R. Matos, M. Kruk, L.P. Mercuri, M. Jaroniec, T. Asefa, N. Coombs, G.A. Ozin, T. Kamiyama, O. Terasaki, Chem. Mater. 14, 1903 (2002)10.1021/cm025513e ↗
18. Z.M. Michalska, Platin. Metals Rev. 18, 65 (1974)10.1595/003214074X1826573 ↗
19. N.K. Thallaj, J. Przybilla, R. Welter, D. Mandon, J. Am. Chem. Soc. 130, 2414 (2008)10.1021/ja710560g ↗
20. R.C. Larock, Comprehensive Organic Transformations, 2nd edn. (Wiley-VCH, New York, 1999), p. 1988
21. J.M. Humphrey, A.R. Chamberlin, Chem. Rev. 97, 2243 (1997)10.1021/cr950005s ↗
22. J.W. Bode, R.M. Fox, K.D. Baucom, Angew. Chem. Int. Ed. 45, 1248 (2006)10.1002/anie.200503991 ↗
23. B.L. Bray, Nat. Rev. Drug Discov. 2, 587 (2003)10.1038/nrd1133 ↗
24. A.L.J. Beckwith, in The Chemistry of Amides: Synthesis of Amides, ed. by J. Zabicky (Wiley-Interscience, New York, 1970), p. 73-18510.1002/9780470771235.ch2 ↗
25. H.R. Sydner, C.T. Elston, J. Am. Chem. Soc. 76, 3039 (1954)
26. C.R. Hauser, C.J. Eby, J. Am. Chem. Soc. 79, 725 (1957)10.1021/ja01560a061 ↗
27. A.R. Katritzky, B. Pilarski, L. Urogdi, Synthesis 949 (1989)10.1055/s-1989-27441 ↗
28. K.L. Breno, M.D. Pluth, D.R. Tyler, Organometallics 22, 1203 (2003)10.1021/om020845e ↗
29. K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. Int. Ed. 43, 1576 (2004)10.1002/anie.200353461 ↗
30. C.W. Leung, W. Zheng, Z. Zhou, Z. Lin, C.P. Lau, Organometallics 27, 4957 (2008)10.1021/om800474w ↗
31. A. Goto, K. Endo, S. Saito, Angew. Chem. Int. Ed. 47, 3607 (2008)10.1002/anie.200800366 ↗
32. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)10.1021/ja974025i ↗
33. Sujandi, S.-E. Park, D.-S. Han, S.-C. Han, M.-J. Jin, T. Ohsuna, Chem. Commun. 4131 (2006)10.1039/b608463j ↗
34. X. Wang, S. Cheng, J.C.C. Chan, J. Phys. Chem. C 111, 2156 (2007)10.1021/jp066924b ↗
35. R. Noyori, M. Aoki, K. Sato, Chem. Commun. 1977 (2003)10.1039/b303160h ↗
36. R. Noyori, Chem. Commun. 1807 (2005)10.1039/b502713f ↗
37. K. Kaczorowska, Z. Kolarska, K. Mitka, P. Kowalski, Tetrahedron 61, 8315 (2005)10.1016/j.tet.2005.05.044 ↗
38. K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73, 6835 (2008)10.1021/jo8010232 ↗
39. K. Bahrami, M.M. Khodaei, M. Sheikh, Arabi. J. Org. Chem. 75, 6208 (2010)10.1021/jo1011784 ↗
40. K. Bahrami, M.M. Khodaei, M. Soheilizad, J. Org. Chem. 74, 9287 (2009)10.1021/jo901924m ↗
41. K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal. Sci. Technol. 1, 389 (2011)
42. T. Ghaffar, A.W. Parkins, J. Mol. Catal. A: Chem. 160, 249 (2000)10.1016/S1381-1169(00)00253-3 ↗
43. K. Manjula, M.A. Pasha, Synth. Commun. 37, 1545 (2007)10.1080/00397910701230147 ↗
44. S. Sahnoun, S. Messaoudi, J.-F. Peyrat, J.-D. Brion, M. Alami, Tetrahedron Lett. 53, 2860 (2012)10.1016/j.tetlet.2012.03.117 ↗
45. A. Khalafi-Nezhad, A. Parhami, M.N. Soltani, Rad, A. Zarea. Tetrahedron Lett. 46, 6879 (2005)10.1016/j.tetlet.2005.08.021 ↗
46. E.V. Bellale, D.S. Bhalerao, K.G. Akamanchi, J. Org. Chem. 73, 9473 (2008)10.1021/jo801580g ↗
47. W.R. Nes, A. Burger, J. Am. Chem. Soc. 72, 5409 (1950)10.1021/ja01168a012 ↗
48. M.M. Lakouraj, K. Bahrami, Indian J. Chem. Sect B 38, 974 (1999)
49. S. Basterfield, M.E. Greig, Canadian J. Res. 8, 450 (1933)10.1139/cjr33-045 ↗
50. D. Breslowg, E. Hulse, A. Matlack, J. Am. Chem. Soc. 79, 3760 (1957)10.1021/ja01571a039 ↗
51. R. Pellegata, A. Italia, M. Villa, Synthesis 517 (1985)10.1055/s-1985-31257 ↗
52. E. Magnien, R. Baltzly, J. Org. Chem. 23, 2029 (1958)10.1021/jo01106a630 ↗
53. K.B. Wiberg, J. Am. Chem. Soc. 76, 3961 (1953)10.1021/ja01112a025 ↗