H5PW10V2O40@VOx/SBA-15-NH2 catalyst for the solventless synthesis of 3-substituted indoles

Functionalization of mesoporous SBA-15 frameworks by transition metal oxides offers a flexible route to fabricate new heterogeneous catalysts. Here, an inorganic-organic hybrid nanoporous catalyst H5PW10V2O40@VOx/SBA-15-NH2, was prepared and utilized as an efficient, eco-friendly, and recyclable cat...

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Bibliographic Details
Published in:Tetrahedron 2017-10, Vol.73 (40), p.5862-5871
Main Authors: Ghohe, Narges Mahdizadeh, Tayebee, Reza, Amini, Mostafa M., Osatiashtiani, Amin, Isaacs, Mark A., Lee, Adam F.
Format: Article
Language:English
Subjects:
3-Substituted indoles
Heteropolyacid
SBA-15
Solventless
Vanadia
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Summary:Functionalization of mesoporous SBA-15 frameworks by transition metal oxides offers a flexible route to fabricate new heterogeneous catalysts. Here, an inorganic-organic hybrid nanoporous catalyst H5PW10V2O40@VOx/SBA-15-NH2, was prepared and utilized as an efficient, eco-friendly, and recyclable catalyst for the one-pot, multi-component synthesis of 3-substituted indoles by indole substitution with aldehydes and malononitrile under solvent-free conditions. Catalysts were prepared by the non-covalent attachment of H5PW10V2O40 to a 3 wt%VOx/SBA-15 nanoporous support through a 3-(triethoxysilyl)propylamine linker. VOx/SBA-15 was prepared by a one-pot hydrothermal synthesis from TEOS and vanadium(V) oxytri-tert-butoxide [VO(O-tBu)3]. The resulting H5PW10V2O40@VOx/SBA-15-NH2 material was characterized by bulk and surface analysis including N2 porosimetry, FE-SEM, XRD, XPS, FT-IR, TGA-DTA, UV–Vis and ICP-OES, evidencing retention of the heteropolyacid Keggin structure. H5PW10V2O40@VOx/SBA-15-NH2 exhibits high activity and excellent yields (70–95%) of 3-substituted indoles under mild conditions, with negligible deactivation. H5PW10V2O40@VOx/SBA-15-NH2 was prepared, characterized, and introduced as an effective catalyst for the one-pot synthesis of 3-substituted indoles. The catalyst could be easily separated without noticeable reduction in activity. [Display omitted] •An inorganic-organic nanoporous material H5PW10V2O40@VOx/SBA-15-NH2 is synthesized.•An efficient and environmentally benign route to 3-substituted indoles is shown.•H5PW10V2O40@VOx/SBA-15-NH2 offers wide scope for a variety of aldehyde substrates.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.08.030