journal article·2023-01

Arylation of indole at C2 catalyzed by palygorskite grafted covalent organic frameworks supported palladium catalyst

Ning Ding, Shang Wu, Qiang Hu, Jutao Liu, Penghui Zhang, Shuaishuai Fu, Huanlei Zhao, Hong Zhang, Fenping Yin, Quanlu Yang

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Abstract

A heterogeneous palladium catalyst, palygorskite grafted covalent organic frameworks supported palladium (Pd-Pal/COF), was successfully prepared by a simple method. A series of C2 aromatic indole derivatives were synthesized under mild reaction conditions. Pd-Pal/COF catalyst can be reused at least 5 times with inappreciable metal leaching. Undoubtedly, facile synthesis, mild reaction conditions, a wide scope of reactants, and recyclability make the catalyst systems potentially useful in organic synthesis. For the synthesized heterogeneous catalysts, palygorskite as a matrix, the unique structure and good dispersion of palygorskite result in the excellent catalytic activity and good cycle stability of the Pd-Pal/COF catalyst, comparing with the traditional clay catalyst. The result further expands the application scope of clay in the catalytic field.
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Research context

OpenAlex topics: Covalent Organic Framework Applications · Metal-Organic Frameworks: Synthesis and Applications · Advanced Photocatalysis Techniques

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (46)

Show source-provided references
1. Clay nanoparticles modified drilling fluids for drilling of deep hydrocarbon wells10.1016/j.clay.2013.10.017 ↗
2. Structure-activity relationships of 2-Aryl-1H-indole inhibitors of the Nor A efflux pump in staphylococcus aureus10.1016/j.bmcl.2008.06.093 ↗
3. C2–H arylation of indoles catalyzed by palladium-containing metal-organic-framework in γ-valerolactone10.1002/cssc.202000378 ↗
4. A new triazine-based covalent organic framework for high-performance capacitive energy storage10.1002/cssc.201601571 ↗
5. Direct C–H bond activation: palladium-on-carbon as a reusable heterogeneous catalyst for C-2 arylation of indoles with arylboronic acids10.1039/D0NJ00735H ↗
6. Synthesis and functionalization of indoles through palladium-catalyzed reactions10.1021/cr040639b ↗
7. Bacteria- adsorbed palygorskite stabilizes the quaternary phosphonium salt with specific-targeting capability, long-term antibacterial activity, and lower cytotoxicity10.1021/la400824f ↗
8. Palladium-catalyzed α-arylation of indolin-3-ones10.1039/D0CC00435A ↗
9. Shape control of platinum and palladium nanoparticles for catalysis10.1039/c0nr00276c ↗
10. Initial structure-activity relationship of a novel class of nonpeptidyl Gn RH receptor antagonists: 2-arylindoles10.1016/S0960-894X(00)00707-1 ↗
11. Tryptophan-replacement and indole-modified apicidins: synthesis of potent and selective antiprotozoal agents10.1016/S0040-4039(00)01363-0 ↗
12. Luminescent covalent organic frameworks containing a homogeneous and heterogeneous distribution of dehydrobenzoannulene vertex units10.1021/jacs.6b06546 ↗
13. Unprecedented C-2 arylation of indole with diazonium salts: syntheses of 2,3-disubstituted indoles and their antimicrobial activity10.1016/j.bmcl.2011.06.081 ↗
14. The atom, the molecule, and the covalent organic framework. 201710.1126/science.aal1585 ↗
15. Palladium catalyzed direct C-2 arylation of indoles10.1016/j.jorganchem.2014.02.017 ↗
16. Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions10.1021/ol801285g ↗
17. A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides10.1021/ja8055358 ↗
18. Methoxy-substituted 3-formyl-2-phenylindoles inhibit tubulin polymerization10.1021/jm980228l ↗
19. Covalent organic frameworks: design, synthesis, and functions10.1021/acs.chemrev.9b00550 ↗
20. Palladium catalyzed P(O)R2 directed C-H arylation to synthesize electron rich polyaromatic monophosphorus ligands10.1039/C3CC49050E ↗
21. Covalent organic frameworks: a materials platform for structural and functional designs10.1038/natrevmats.2016.68 ↗
22. simple indole alkaloids and those with a nonrearranged monoterpenoid unit10.1039/b820693g ↗
23. Synthesis and characterization of high siliceous ZSM-5 zeolite from acid-treated palygorskite10.1016/j.powtec.2013.10.020 ↗
24. Covalent organic frameworks: chemistry beyond the structure10.1021/jacs.8b10334 ↗
25. Biomedical importance of indoles10.3390/molecules18066620 ↗
26. P(O)R2-directed enantioselective C-H olefination toward chiral atropoisomeric phosphine-olefin compounds10.1021/acs.orglett.7b00608 ↗
27. Effect of palygorskite clay on pyrolysis of rape straw: an in situ catalysis study10.1016/j.jcis.2013.11.041 ↗
28. Room-temperature palladium (II)-catalyzed direct 2-arylation of indoles with tetraarylstannanes10.1055/s-0040-1707196 ↗
29. Palygorskitepoly (o-phenylenediamine) nanocomposite: an enhanced electrochemical platform for glucose biosensing10.1016/j.clay.2013.10.013 ↗
30. Porous, crystalline, covalent organic frameworks10.1126/science.1120411 ↗
31. P(O)R2 directed Pd(II)-catalyzed C(sp2)-H acylation10.1039/C4QO00005F ↗
32. Development of reusable palladium catalysts supported on hydrogen titanate nanotubes for the Heck reaction10.1016/j.jcat.2016.07.019 ↗
33. Evaluation of Fe(III) adsorption onto palygorskite surfaces10.1016/j.apsusc.2013.05.113 ↗
34. Multifunctional catalysts based on palladium nanoparticles supported on functionalized halloysites: applications in catalytic C-C coupling, selective oxidation and dehalogenation reactions
35. can the observed changes in the size or shape of a colloidal nanocatalyst reveal the nanocatalysis mechanism type: homogeneous or heterogeneous10.1007/s11244-008-9057-4 ↗
36. Palladium-catalyzed arylation and heteroarylation of indolizines10.1021/ol049866q ↗
37. Highly functionalized biaryls via Suzuki-Miyaura cross-coupling catalyzed by Pd@MOF under batch and continuous flow regimes10.1002/cssc.201402858 ↗
38. Pyridylmethylamine–palladium catalytic systems: a selective alternative in the C−H arylation of indole10.1002/cctc.201601275 ↗
39. Imidazolium-salt-functionalized covalent organic frameworks for highly efficient catalysis of CO2 conversion10.1002/cssc.201900570 ↗
40. One-pot arylative benzannulation of 2-carbonyl-3-propargyl indoles with boronic acids leading to arylated carbazoles10.1021/acs.joc.0c02601 ↗
41. Palladium-catalyzed arylative benzannulation of 4-alkynyl-3-alkenyl indoles with arylboronic acids to benzo [cd] indoles10.1016/j.cdc.2022.100865 ↗
42. Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications10.1039/C5CS00878F ↗
43. Pd(II)-catalyzed Ph2(O)P-directed C-H olefination toward phosphine-alkene ligands10.1021/ol402577p ↗
44. Palladium-catalyzed arylation/heteroarylation of indoles: access to 2, 3-functionalized indolines10.1021/acs.orglett.8b03310 ↗
45. Palladium-catalyzed R2(O)P directed C(sp2)-H acetoxylation10.1039/C4CC01238K ↗
46. Palladium-catalyzed direct C-2 arylation of indoles with potassium aryltrifluoroborate salts10.1021/jo801371w ↗