H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles

Reza Tayebee; Adam Lee; Lucia Frattini; Shahrebano Rostami

doi:10.3390/catal9050409

H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles

Reza Tayebee, Adam Lee, Lucia Frattini, Shahrebano Rostami

Chemical Engineering & Applied Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A family of silica-supported H3PW12O40 (HPW) solid acid catalysts was prepared by wet impregnation of mesoporous SBA-15 and investigated for the solventless synthesis of 3-substituted indoles under mild conditions. Mesoporous SBA-15 facilitated a high dispersion of immobilised H3PW12O40, significantly improving the catalytic efficiency of the heteropolyacid for the desired multi-component transformation. The yield of 3-substituted indoles strongly correlated with HPW loading (which spanned 3.2–51.6 wt %) and corresponding acid strength; the 51.6 wt % HPW/SBA-15 delivered 81% yield of 2-[(1H-indol-3-yl)(phenyl)methyl]malononitrile, approximately five times greater than that of the unsupported HPW, and exhibited a broad substrate scope for aromatic aldehydes.

Original language	English
Article number	409
Journal	Catalysts
Volume	9
Issue number	5
DOIs	https://doi.org/10.3390/catal9050409
Publication status	Published - 30 Apr 2019

Bibliographical note

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Keywords

3-substituted indole
Condensation
H PW O
SBA-15

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H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
Final published version, 358 KBLicence: CC BY 3.0

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title = "H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles",

abstract = "A family of silica-supported H3PW12O40 (HPW) solid acid catalysts was prepared by wet impregnation of mesoporous SBA-15 and investigated for the solventless synthesis of 3-substituted indoles under mild conditions. Mesoporous SBA-15 facilitated a high dispersion of immobilised H3PW12O40, significantly improving the catalytic efficiency of the heteropolyacid for the desired multi-component transformation. The yield of 3-substituted indoles strongly correlated with HPW loading (which spanned 3.2–51.6 wt %) and corresponding acid strength; the 51.6 wt % HPW/SBA-15 delivered 81% yield of 2-[(1H-indol-3-yl)(phenyl)methyl]malononitrile, approximately five times greater than that of the unsupported HPW, and exhibited a broad substrate scope for aromatic aldehydes.",

keywords = "3-substituted indole, Condensation, H PW O, SBA-15",

author = "Reza Tayebee and Adam Lee and Lucia Frattini and Shahrebano Rostami",

note = "This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).",

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T1 - H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles

AU - Tayebee, Reza

AU - Lee, Adam

AU - Frattini, Lucia

AU - Rostami, Shahrebano

N1 - This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

PY - 2019/4/30

Y1 - 2019/4/30

N2 - A family of silica-supported H3PW12O40 (HPW) solid acid catalysts was prepared by wet impregnation of mesoporous SBA-15 and investigated for the solventless synthesis of 3-substituted indoles under mild conditions. Mesoporous SBA-15 facilitated a high dispersion of immobilised H3PW12O40, significantly improving the catalytic efficiency of the heteropolyacid for the desired multi-component transformation. The yield of 3-substituted indoles strongly correlated with HPW loading (which spanned 3.2–51.6 wt %) and corresponding acid strength; the 51.6 wt % HPW/SBA-15 delivered 81% yield of 2-[(1H-indol-3-yl)(phenyl)methyl]malononitrile, approximately five times greater than that of the unsupported HPW, and exhibited a broad substrate scope for aromatic aldehydes.

AB - A family of silica-supported H3PW12O40 (HPW) solid acid catalysts was prepared by wet impregnation of mesoporous SBA-15 and investigated for the solventless synthesis of 3-substituted indoles under mild conditions. Mesoporous SBA-15 facilitated a high dispersion of immobilised H3PW12O40, significantly improving the catalytic efficiency of the heteropolyacid for the desired multi-component transformation. The yield of 3-substituted indoles strongly correlated with HPW loading (which spanned 3.2–51.6 wt %) and corresponding acid strength; the 51.6 wt % HPW/SBA-15 delivered 81% yield of 2-[(1H-indol-3-yl)(phenyl)methyl]malononitrile, approximately five times greater than that of the unsupported HPW, and exhibited a broad substrate scope for aromatic aldehydes.

KW - 3-substituted indole

KW - Condensation

KW - H PW O

KW - SBA-15

UR - https://www.mdpi.com/2073-4344/9/5/409

UR - http://www.scopus.com/inward/record.url?scp=85067583797&partnerID=8YFLogxK

U2 - 10.3390/catal9050409

DO - 10.3390/catal9050409

M3 - Article

SN - 2073-4344

VL - 9

JO - Catalysts

JF - Catalysts

IS - 5

M1 - 409

ER -

H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles

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Keywords

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