Collect. Czech. Chem. Commun.
2011, 76, 1979-1990
https://doi.org/10.1135/cccc2011131
Published online 2012-01-31 08:36:38
Formylation of amines and alcohols using aminopropylated mesoporous SBA-15 silica (APMS) as an efficient and recyclable catalyst
Reihaneh Malakootia,*, Sara Sobhanib,*, Nasrin Razavib, Soheila Shafieia and Rezvan Mokhtaria
a Nanochemistry Research Laboratory, Department of Chemistry, University of Birjand, Birjand 414, Iran
b Department of Chemistry, College of Sciences, Birjand University, Birjand 414, Iran
References
1. A., Meth-Cohn O.: J. Chem. Soc., Chem. Commun. 1995, 13, 1319.
<https://doi.org/10.1039/c39950001319>
2. B. C., Bednarz M. S., Zhao R., Sundeen J. E., Chen P., Shen Z., Skoumbourdis A. P., Barrish J. C.: Tetrahedron Lett. 2000, 41, 5453.
<https://doi.org/10.1016/S0040-4039(00)00910-2>
3. K., Nagato S., Kawakita M., Morikawa O., Konishi H.: Chem. Lett. 1995, 24, 575.
<https://doi.org/10.1246/cl.1995.575>
4. A., Ito S., Hayashi S., Fujii T.: Bull. Chem. Soc. Jpn. 1995, 68, 3573.
<https://doi.org/10.1246/bcsj.68.3573>
5. B. B., Baskaran S., Rao B. S., Reddy B. Y., Rao I. N.: Tetrahedron Lett. 1999, 40, 4855.
<https://doi.org/10.1016/S0040-4039(99)00893-X>
6. G. R., Kalnins M. V., Liu T. M. H., Thomas E. G., Parent K.: J. Org. Chem. 1961, 26, 2563.
<https://doi.org/10.1021/jo01351a623>
7. S., Nishio K.: J. Org. Chem. 1994, 59, 6620.
<https://doi.org/10.1021/jo00101a021>
8. S., Yasuda M., Hachiya I.: Chem. Lett. 1996, 25, 407.
<https://doi.org/10.1246/cl.1996.407>
9. I. M., Earle M. J., Heaney H., Shuhaibar K. F.: Tetrahedron 1993, 49, 4015.
<https://doi.org/10.1016/S0040-4020(01)89915-4>
10. Y., Cai L.: Tetrahedron Lett. 1997, 38, 5423.
<https://doi.org/10.1016/S0040-4039(97)01206-9>
11. R., Ciambecchini U., Crestini C., Costanzo G., Negri R., Di Mauro E.: Chem. Biochem. 2003, 4, 514.
12. H., Kobayashi Y., Kimachi T., Yasui Y., Takemoto Y.: J. Organomet. Chem. 2011, 696, 42.
<https://doi.org/10.1016/j.jorganchem.2010.06.021>
13. J., Laur J.: Synthesis 1982, 11, 979.
<https://doi.org/10.1055/s-1982-30034>
14a. Green T. W., Wuts P. G. M.: Protective Groups in Organic Synthesis, 3rd ed., Vol. 76, p. 708. Wiley–Interscience, New York 1999.
14b. J. C., Yang D. D. H.: J. Am. Chem. Soc. 1958, 80, 1154.
<https://doi.org/10.1021/ja01538a036>
15. F. F., Lu C.-J.: J. Am. Chem. Soc. 1952, 74, 3933.
<https://doi.org/10.1021/ja01135a503>
16a. L., Sheykhan M., Heydari H., Faraji M., Yamini Y.: Appl. Catal., A 2010, 377, 64.
16b. M., Sharghi H.: J. Org. Chem. 2006, 71, 6652.
<https://doi.org/10.1021/jo060847z>
16c. H., Iranpoor N., Farahi S.: J. Mol. Catal. A: Chem. 2008, 289, 61.
<https://doi.org/10.1016/j.molcata.2008.04.010>
16d. , Saberi D.: Tetrahedron Lett. 2009, 50, 5210.
<https://doi.org/10.1016/j.tetlet.2009.06.140>
16e. J.-G., Doo Ok.: Synlett 2010, 2093.
16f. B., Krishnaiah M., Balasubramanayam P., Veeranjaneyulu B., Kumar D. N.: Tetrahedron Lett. 2008, 49, 2225.
<https://doi.org/10.1016/j.tetlet.2008.02.050>
17a. H. L.: J. Org. Chem. 1971, 36, 3238.
<https://doi.org/10.1021/jo00820a603>
17b. L., Laszlo O.: Synthesis 1987, 510.
<https://doi.org/10.1055/s-1987-27987>
17c. M., Bruneaum C., Dixneuf P. H.: J. Chem. Soc., Perkin Trans. 1, 1991, 1197.
<https://doi.org/10.1039/p19910001197>
17d. W., Deutsch J., Vieth S., Niclas H.-J.: Synthesis 1996, 37.
18. M., Ishino Y., Minakata S., Komatsu M.: Synthesis 2003, 2317.
19. P. G., Kumar G. D. K., Baskaran S.: Tetrahedron 2000, 41, 9149.
20. D. L., Giacomelli G., Porcheddu A., Salaris M.: Synlett 2004, 2570.
21. B., Danks T. N., Wagner G.: Tetrahedron Lett. 2005, 46, 955.
<https://doi.org/10.1016/j.tetlet.2004.12.044>
22a. X. G., Lin K. S. K., Chan J. C. C., Cheng S.: Chem. Commun. 2004, 2762.
<https://doi.org/10.1039/b408022j>
22b. R. M., Čejka J.: Top. Catal. 2010, 53, 141.
<https://doi.org/10.1007/s11244-009-9419-6>
22c. L., Wang Y., Wang J., Huang L., Shi L., Fan X., Zou Z., Yu T., Zhu M., Li Z.: Inorg. Chem. 2006, 45, 6844.
<https://doi.org/10.1021/ic0516562>
22d. A., Schuth F.: Micro. Meso. Mat. 2005, 77, 1.
<https://doi.org/10.1016/j.micromeso.2004.06.030>
22e. V., Pérez-Mayoral E., Martín-Aranda R. M., Zienkiewicz Z., Sobczak I., Ziolek M.: Top. Catal. 2010, 53, 179.
<https://doi.org/10.1007/s11244-009-9422-y>
23a. D., Fajula F., Nagy J. B., Deroide B., Verhoef M. J., Veum L., Peters J. A., Van Bekkum H.: Appl. Catal., A 2001, 213, 73.
23b. D. J., Jackson D. B.: Chem. Commun. 1997, 1781.
<https://doi.org/10.1039/a704156j>
24a. Sobhani S., Hasaninejad A. R., Faal Maleki M., Pakdin Parizi Z.: Synth. Commun. 2011
<https://doi.org/10.1080/00397911.2011.555589>
24b. S., Pakdin Parizi Z., Rezazadeh S.: J. Organomet. Chem. 2011, 696, 813.
<https://doi.org/10.1016/j.jorganchem.2010.10.015>
24c. S., Rezazadeh S.: Synlett 2010, 1485.
<https://doi.org/10.1055/s-0029-1220069>
25. D., Feng J., Hu Q., Melosh N., Fredrickson G. H., Chmelka B. F., Stucky S. D.: Science 1998, 279, 548.
<https://doi.org/10.1126/science.279.5350.548>
26. V., Badaničová M., Halamová D., Čejka J., Zukal A., Murafa N., Goerigk G.: Chem. Eng. J. 2008, 144, 336.
<https://doi.org/10.1016/j.cej.2008.07.025>
27. W. H., Lu X. B., Xiu J. H., Hua Z. L., Zhang L. X., Robertson M., Shi J. L., Yan D. S., Holmes J. D.: Adv. Funct. Mater. 2004, 14, 544.
<https://doi.org/10.1002/adfm.200305001>
28. R., Veisi H., Amiri M., Chegini M., Karimi M., Akbari S., Sedrpoushan A.: S. Afri. J. Chem. 2009, 62, 39.
29. Shintani T., Maeda M., Ohara T.: Jpn. Kokai Tokkyo Koho JP 2003, 267933; Chem. Abstr. 2003, 139, 853.
30. Chem J. K., Hyman J. M., Ocasio C. A.: PCT Int. Appl. WO 2009, 102864; Chem. Abstr. 2009, 151, 2153.
31. A., Ravi Kumar A., Sathaiah G., Luke Paul V., Madabhushi S., Shanthan Rao P.: Tetrahedron Lett. 2009, 50, 7099.
<https://doi.org/10.1016/j.tetlet.2009.10.006>
32. M., Arrigo P. D., Fasoli E., Servi S., Tessaro D., Canvotti F., Del Corona L.: Tetrahedron: Asymmetry 2003, 14, 3189.
33. A., Reddy B. V. S., Premalatha K., Reddy S. S., Yadav J. S.: Catal. Lett. 2009, 131, 480.
<https://doi.org/10.1007/s10562-009-9927-9>
34. B., Swaminathan M.: J. Mol. Catal. A: Chem. 2011, 334, 98.
<https://doi.org/10.1016/j.molcata.2010.11.002>
35. R. I., Zhenodarova S. M.: Synthesis 1975, 222.
<https://doi.org/10.1055/s-1975-23714>
36a. R. N., Meher N. K.: Tetrahedron 2002, 58, 2997.
<https://doi.org/10.1016/S0040-4020(02)00185-0>
36b. N., Firouzabadi H., Jamalian A.: Tetrahedron Lett. 2005, 46, 7963.
<https://doi.org/10.1016/j.tetlet.2005.09.078>
36c. H., Morohashi K., Sakai H., Suzuki T., Ando M.: Tetrahedron 1998, 54, 5845.
<https://doi.org/10.1016/S0040-4020(98)00255-5>
37a. N., Firouzabadi H., Zolfigol M. A.: Synth. Commun. 1998, 28, 1923.
<https://doi.org/10.1080/00397919808007166>
37b. M. C., Prince M. C.: Tetrahedron Lett. 1994, 35, 2463.
<https://doi.org/10.1016/S0040-4039(00)77144-9>
37c. T., Matsumoto T., Kawada M., Tsuji J.: J. Org. Chem. 1992, 57, 1326.
<https://doi.org/10.1021/jo00031a005>
38. , Zolfigol M. A., Saberi D., Khonbazi M.: Chin. J. Chem. 2009, 27, 1548.
<https://doi.org/10.1002/cjoc.200990261>
39. M. H., Tangestaninejad S. H., Mirkhani V., Yadollahi B.: Tetrahedron 2001, 57 8333.
<https://doi.org/10.1016/S0040-4020(01)00806-7>
40. F., Zolfigol M. A., Mohammadi K.: Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1617.
<https://doi.org/10.1080/10426500307877>
41. J. Y., Huang H. G., Lin K. Y., Liu Q. P., Sun Y. M., Xu G. Q.: Surf. Sci. 2004, 549, 255.
<https://doi.org/10.1016/j.susc.2003.12.011>

