An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

Venu Boosa; Vishali Bilakanti; Vijay Kumar Velisoju; Naresh Gutta; Sreedhar Inkollu; Venugopal Akula

doi:10.1016/j.mcat.2017.11.007

An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

Venu Boosa, Vishali Bilakanti, Vijay Kumar Velisoju, Naresh Gutta, Sreedhar Inkollu, Venugopal Akula

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

15 Scopus citations

Abstract

The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.

Original language	English (US)
Pages (from-to)	43-51
Number of pages	9
Journal	Molecular Catalysis
Volume	445
DOIs	https://doi.org/10.1016/j.mcat.2017.11.007
State	Published - Feb 1 2018
Externally published	Yes

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10.1016/j.mcat.2017.11.007

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title = "An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst",

abstract = "The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.",

author = "Venu Boosa and Vishali Bilakanti and Velisoju, {Vijay Kumar} and Naresh Gutta and Sreedhar Inkollu and Venugopal Akula",

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doi = "10.1016/j.mcat.2017.11.007",

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T1 - An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

AU - Boosa, Venu

AU - Bilakanti, Vishali

AU - Velisoju, Vijay Kumar

AU - Gutta, Naresh

AU - Inkollu, Sreedhar

AU - Akula, Venugopal

N1 - Generated from Scopus record by KAUST IRTS on 2023-10-23

PY - 2018/2/1

Y1 - 2018/2/1

N2 - The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.

AB - The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.

UR - https://linkinghub.elsevier.com/retrieve/pii/S2468823117305990

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DO - 10.1016/j.mcat.2017.11.007

M3 - Article

SN - 2468-8231

VL - 445

SP - 43

EP - 51

JO - Molecular Catalysis

JF - Molecular Catalysis

ER -

An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

Abstract

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