Highly active recyclable SBA-15-EDTA-Pd catalyst for Mizoroki-Heck, Stille and Kumada C–C coupling reactions
Source abstract
Abstract
Highly efficient SBA-15-EDTA-Pd(11) heterogeneous catalyst was synthesized by covalent anchoring Pd-EDTA complex over organo-modified surface of SBA-15. SBA-15-EDTA-Pd(11) catalyst was found to exhibit excellent catalytic activity in appreciable yield for Heck, Stille and Kumada cross-coupling reactions. Catalytic system exhibited excellent activity for completion of reaction, isolation, Pd loading (0.87 mmol%) and yields of products as compared to earlier reported heterogeneous supported Pd catalysts. Covalently anchored heterogeneous SBA-15-EDTA-Pd(11) catalyst can be recycled for more than five times without noticeable loss in activity and selectivity.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Catalytic Cross-Coupling Reactions · Mesoporous Materials and Catalysis · Polyoxometalates: Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (38)
Show source-provided references
1. M. Lamblin, L. Nassar-Hardy, J.-C. Hierso, E. Fouquet, F.-X. Felpin, Adv. Synth. Catal. 352, 33–79 (2010)10.1002/adsc.200900765 ↗
2. A. Pal, R. Ghosh, N.N. Adarsh, A. Sarkar, Tetrahedron 66, 5451–5458 (2010)10.1016/j.tet.2010.05.026 ↗
3. A.C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 687, 403–409 (2003)10.1016/S0022-328X(03)00723-X ↗
4. I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009–3066 (2000)10.1021/cr9903048 ↗
5. S.P. Stanforth, Tetrahedron 54, 263–303 (1998)10.1016/S0040-4020(97)10233-2 ↗
6. A. Dahan, M. Portnoy, Org. Lett. 5, 1197–1200 (2003)10.1021/ol0340181 ↗
7. A. Cwik, Z. Hell, F. Figueras, Adv. Synth. Catal. 348, 523–530 (2006)10.1002/adsc.200505225 ↗
8. B.M. Choudary, S. Madhi, N.S. Chowdari, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 124, 14127–14136 (2002)10.1021/ja026975w ↗
9. S. Rostamnia, E. Doustkhah, RSC Adv. 4, 28238–28248 (2014)10.1039/C4RA03773A ↗
10. A. Dandapat, D. Jana, G. De, Appl. Catal. A Gen. 396, 34–39 (2011)10.1016/j.apcata.2011.01.032 ↗
11. J.Y. Ying, C.P. Mehnert, M.S. Wong, Angew. Chem. Int. Ed. 38, 56–77 (1999)10.1002/(SICI)1521-3773(19990115)38:1/2<56::AID-ANIE56>3.0.CO;2-E ↗
12. D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279, 548–552 (1998)10.1126/science.279.5350.548 ↗
13. R.I. Kureshy, I. Ahmad, N.-U.H. Khan, S.H.R. Abdi, K. Pathak, R.V. Jasra, Tetrahedron Asymm. 16, 3562–3569 (2005)10.1016/j.tetasy.2005.09.022 ↗
14. P. Sharma, A.P. Singh, Catal. Sci. Technol. 4, 2978–2989 (2014)10.1039/C4CY00144C ↗
15. D.N. Korolev, N.A. Bumagin, Tetrahedron Lett. 46, 5751–5754 (2005)10.1016/j.tetlet.2005.06.085 ↗
16. P. Sharma, A.P. Singh, RSC Adv. 4, 58467–58475 (2014)10.1039/C4RA10002F ↗
17. A. Modak, J. Mondal, M. Sasidharan, A. Bhaumik, Green Chem. 13, 1317–1331 (2011)10.1039/c1gc15045f ↗
18. T.M. Shaikh, F.-E. Hong, Beilstein J. Org. Chem. 9, 1578–1588 (2013)10.3762/bjoc.9.180 ↗
19. J. McNulty, P. Das, Eur. J. Org. Chem. 2009, 4031–4035 (2009)10.1002/ejoc.200900634 ↗
20. P. Sun, Y. Zhu, H. Yang, H. Yan, L. Lu, X. Zhang, J. Mao, Org. Biomol. Chem. 10, 4512–4515 (2012)10.1039/c2ob25462j ↗
21. R. Cella, H.A. Stefani, Tetrahedron 62, 5656–5662 (2006)10.1016/j.tet.2006.03.090 ↗
22. Z. Shu, Y. Zhou, Y. Zhang, J. Wang, Org. Chem. Front. 1, 1123–1127 (2014)10.1039/C4QO00218K ↗
23. M. Amini, M. Bagherzadeh, Z. Moradi-Shoeili, D.M. Boghaei, RSC Adv. 2, 12091–12095 (2012)10.1039/c2ra21459h ↗
24. S. Sobhani, Z.M. Falatooni, S. Asadi, M. Honarmand, Catal. Lett. 146, 255–268 (2016)10.1007/s10562-015-1636-y ↗
25. S.-L. Huang, A.-Q. Jia, G.-X. Jin, Chem. Commun. 49, 2403–2405 (2013)10.1039/c3cc38714c ↗
26. J.D. Senra, L.F.B. Malta, M.E.H.M. da Costa, R.C. Michel, L.C.S. Aguiar, A.B.C. Simas, O.A.C. Antunes, Adv. Synth. Catal. 351, 2411–2422 (2009)10.1002/adsc.200900348 ↗
27. D. Wang, W. Liu, F. Bian, W. Yu, New J. Chem. 39, 2052–2059 (2015)10.1039/C4NJ01581A ↗
28. J.E. Moses, J.E. Baldwin, S. Bruckner, S.J. Eade, R.M. Adlington, Org. Biomol. Chem. 1, 3670–3684 (2003)10.1039/B306933H ↗
29. H. Lebel, M. Davi, Adv. Synth. Catal. 350, 2352–2358 (2008)10.1002/adsc.200800381 ↗
30. K.V. Kutonova, M.E. Trusova, A.V. Stankevich, P.S. Postnikov, V.D. Filimonov, Beilstein J. Org. Chem. 11, 358–362 (2015)10.3762/bjoc.11.41 ↗
31. J. Yang, L. Wang, Dalton Trans. 41, 12031–12037 (2012)10.1039/c2dt31174g ↗
32. B. Tao, D.W. Boykin, J. Org. Chem. 69, 4330–4335 (2004)10.1021/jo040147z ↗
33. Z. Du, W. Zhou, F. Wang, J.-X. Wang, Tetrahedron 67, 4914–4918 (2011)10.1016/j.tet.2011.04.093 ↗
34. L. Wang, Chin. J. Chem. 24, 770–774 (2006)10.1002/cjoc.200690146 ↗
35. L. Ackermann, A.R. Kapdi, C. Schulzke, Org. Lett. 12, 2298–2301 (2010)10.1021/ol100658y ↗
36. C. Yu, B. Tian, J. Fan, G.D. Stucky, D. Zhao, J. Am. Chem. Soc. 124, 4556–4557 (2002)10.1021/ja025548f ↗
37. J. Huang, F. Zhang, Appl. Organomet. Chem. 24, 767–773 (2010)10.1002/aoc.1696 ↗
38. X.J. Feng, M. Yan, X. Zhang, M. Bao, Chin. Chem. Lett. 22, 643–646 (2011)10.1016/j.cclet.2010.12.044 ↗