Synthesis of mesoporous zirconium-containing silicates and their application for catalytic asymmetric addition of diethylzinc to aldehydes
Source abstract
Abstract
A series of mesoporous zirconium-containing silicates were prepared in sol–gel, which were further functionalized by chiral sulfonyl chloride and proline for catalytic asymmetric addition of diethylzinc to aldehydes. These materials had good porosities, hexagonal symmetries and internal chiralities. Moreover, significant morphological variations were observed when preparative conditions were changed. These materials also showed good to excellent enantioselectivities in catalysis, and there was chiral induction synergy between silicate matrix and attached ligand. Recycling of catalyst was tested, and promising results were obtained. This study would contribute to the design of mesoporous chiral catalysts.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Mesoporous Materials and Catalysis · Asymmetric Hydrogenation and Catalysis · Polyoxometalates: Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (47)
Show source-provided references
1. T. Tsubogo, T. Ishiwata, S. Kobayashi, Angew. Chem. Int. Ed. 52, 6590–6604 (2013)10.1002/anie.201210066 ↗
2. A. Lumbroso, M.L. Cooke, B. Breit, Angew. Chem. Int. Ed. 52, 1890–1932 (2013)10.1002/anie.201204579 ↗
3. L. Pu, H. Yu, Chem. Rev. 101, 757–824 (2001)10.1021/cr000411y ↗
4. M. Fontes, X. Verdaguer, L. Solà, A. Vidal-Ferran, K.S. Reddy, A. Riera, M.A. Pericàs, Org. Lett. 4, 2381–2383 (2002)10.1021/ol0260268 ↗
5. A.L. Braga, M.W. Paixão, D.S. Lüdtke, C.C. Silveira, O.E.D. Rodrigues, Org. Lett. 5, 2635–2638 (2003)10.1021/ol034773e ↗
6. H. Kotsuki, M. Wakao, H. Hayakawa, T. Shimanouchi, M. Shiro, J. Org. Chem. 61, 8915–8920 (1996)10.1021/jo961388c ↗
7. T. Mino, A. Suzuki, M. Yamashita, S. Narita, Y. Shirae, M. Sakamoto, T. Fujita, J. Organomet. Chem. 691, 4297–4303 (2006)10.1016/j.jorganchem.2006.07.006 ↗
8. F. Faigl, Z. Erdélyi, S. Deák, M. Nyerges, B. Mátravölgyi, Tetrahedron Lett. 55, 6891–6894 (2014)10.1016/j.tetlet.2014.10.101 ↗
9. F. Li, H. Huang, H. Zong, G. Bian, L. Song, Tetrahedron Lett. 56, 2071–2076 (2015)10.1016/j.tetlet.2015.03.020 ↗
10. H. Du, K. Ding, Org. Lett. 5, 1091–1093 (2003)10.1021/ol034143c ↗
11. F. Jiang, B. Liu, Z. Dong, J. Li, J. Organomet. Chem. 692, 4377–4380 (2007)10.1016/j.jorganchem.2007.07.003 ↗
12. K. Soai, M. Watanabe, A. Yamamoto, J. Org. Chem. 55, 4832–4835 (1990)10.1021/jo00303a014 ↗
13. T. Kawasaki, Y. Araki, K. Hatase, K. Suzuki, A. Matsumoto, T. Yokoi, Y. Kubota, T. Tatsumi, K. Soai, Chem. Commun. 51, 8742–8744 (2015)10.1039/C5CC01750E ↗
14. S. Jarzyński, M. Rachwalski, A.M. Pieczonka, Z. Wujkowska, S. Leśniak, Tetrahedron Asymmetry 26, 924–927 (2015)10.1016/j.tetasy.2015.07.010 ↗
15. V. Angamuthu, D.-F. Tai, Appl. Catal. A Gen. 506, 254–260 (2015)10.1016/j.apcata.2015.09.006 ↗
16. M. Heidlindemann, G. Rulli, A. Berkessel, W. Hummel, H. Gröger, ACS Catal. 4, 1099–1103 (2014)10.1021/cs4010387 ↗
17. T.T. Adint, C.R. Landis, J. Am. Chem. Soc. 136, 7943–7953 (2014)10.1021/ja501568k ↗
18. Y.-C. Chen, T.-F. Wu, L. Jiang, J.-G. Deng, H. Liu, J. Zhu, Y.-Z. Jiang, J. Org. Chem. 70, 1006–1010 (2005)10.1021/jo048317v ↗
19. G. Chollet, F. Rodriguez, E. Schulz, Org. Lett. 8, 539–542 (2006)10.1021/ol053036a ↗
20. M. Moliner, A. Corma, Chem. Mater. 24, 4371–4375 (2012)10.1021/cm302509m ↗
21. C.I. Fernandes, M.S. Saraiva, T.G. Nunes, P.D. Vaz, C.D. Nunes, J. Catal. 309, 21–32 (2014)10.1016/j.jcat.2013.08.032 ↗
22. K. Soai, S. Niwa, Chem. Rev. 92, 833–856 (1992)10.1021/cr00013a004 ↗
23. L. Ramos, L.M. Hernández, M.J. González, Anal. Chem. 71, 70–77 (1999)10.1021/ac9806153 ↗
24. J. Zhang, L. Li, Y. Li, G. Zhang, A. Zheng, J. Zhang, Y. Sun, Catal. Lett. 145, 1148–1161 (2015)10.1007/s10562-015-1510-y ↗
25. T. Lu, X. Yao, M.G.Q. Lu, Y. He, J. Porous Mater. 17, 123–131 (2010)10.1007/s10934-009-9272-9 ↗
26. O. Pauvert, F. Fayon, A. Rakhmatullin, S. Krämer, M. Horvatić, D. Avignant, C. Berthier, M. Deschamps, D. Massiot, C. Bessada, Inorg. Chem. 48, 8709–8717 (2009)10.1021/ic9007119 ↗
27. A. Ramanathan, H. Zhu, R. Maheswari, B. Subramaniam, Chem. Eng. J. 278, 113–121 (2015)10.1016/j.cej.2014.11.099 ↗
28. Y. Zhu, G. Chuah, S. Jaenicke, J. Catal. 227, 1–10 (2004)10.1016/j.jcat.2004.05.037 ↗
29. P. Kaminski, M. Ziolek, J. Catal. 312, 249–262 (2014)10.1016/j.jcat.2014.02.005 ↗
30. D. Nedumaran, A. Pandurangan, Microporous Mesoporous Mater. 169, 25–34 (2013)10.1016/j.micromeso.2012.09.026 ↗
31. G.R. Pettit, S.B. Singh, D.L. Herald, P. Lloyd-Williams, D. Kantoci, D.D. Burkett, J. Barkóczy, F. Hogan, T.R. Wardlaw, J. Org. Chem. 59, 6287–6295 (1994)10.1021/jo00100a034 ↗
32. Z. Guo, Y. Du, Y. Chen, S.-C. Ng, Y. Yang, J. Phys. Chem. C 114, 14353–14361 (2010)10.1021/jp1059825 ↗
33. Y. Han, L. Zhao, J.Y. Ying, Adv. Mater. 19, 2454–2459 (2007)10.1002/adma.200602703 ↗
34. H. Zhang, Y. Zhang, C. Li, J. Catal. 238, 369–381 (2006)10.1016/j.jcat.2005.12.023 ↗
35. M.I. Coahuila Hernández, M.A. García Sánchez, A.M. Soto Estrada, A. Campero, J. Solgel Sci. Technol. 37, 117–120 (2006)10.1007/s10971-006-6429-8 ↗
36. A.I. Bortun, L.N. Bortun, A. Clearfield, Chem. Mater. 9, 1854–1864 (1997)10.1021/cm9701419 ↗
37. A. Lazar, P. Sharma, A.P. Singh, Microporous Mesoporous Mater. 170, 331–339 (2013)10.1016/j.micromeso.2012.12.014 ↗
38. Q. Pan, A. Ramanathan, W.K. Snavely, R.V. Chaudhari, B. Subramaniam, Ind. Eng. Chem. Res. 52, 15481–15487 (2013)10.1021/ie4019484 ↗
39. K. Yu, Z. Gu, R. Ji, L.-L. Lou, F. Ding, C. Zhang, S. Liu, J. Catal. 252, 312–320 (2007)10.1016/j.jcat.2007.09.009 ↗
40. N. Hiyoshi, Appl. Catal. A Gen. 419–420, 164–169 (2012)10.1016/j.apcata.2012.01.026 ↗
41. K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquérol, T. Siemieniewska, Pure Appl. Chem. 57, 603–619 (1985)10.1351/pac198557040603 ↗
42. R. Fu, N. Yoshizawa, M.S. Dresselhaus, G. Dresselhaus, J.H. Satcher Jr., T.F. Baumann, Langmuir 18, 10100–10104 (2002)10.1021/la020556v ↗
43. S.P. Chenakin, G. Melaet, R. Szukiewicz, N. Kruse, J. Catal. 312, 1–11 (2014)10.1016/j.jcat.2014.01.008 ↗
44. R.I. Kureshy, I. Ahmad, K. Pathak, N.H. Khan, S.H.R. Abdi, J.K. Prathap, R.V. Jasra, Chirality 19, 352–357 (2007)10.1002/chir.20387 ↗
45. S.-W. Kang, D.-H. Ko, K.H. Kim, D.-C. Ha, Org. Lett. 5, 4517–4519 (2003)10.1021/ol0358511 ↗
46. A. Osatiashtiani, A.F. Lee, M. Granollers, D.R. Brown, L. Olivi, G. Morales, J.A. Melero, K. Wilson, ACS Catal. 5, 4345–4352 (2015)10.1021/acscatal.5b00965 ↗
47. L. Li, F. Guan, X. Li, C. Fan, A. Zheng, B. Huang, J. Zhang, Y. Sun, J. Mol. Catal. A Chem. 414, 167–176 (2016)10.1016/j.molcata.2016.01.017 ↗