Larock indole synthesis using palladium complexes immobilized onto mesoporous silica

Nelly Batail; Anissa Bendjeriou; Laurent Djakovitch; Véronique Dufaud

doi:10.1016/j.apcata.2010.08.046

Larock indole synthesis using palladium complexes immobilized onto mesoporous silica

Nelly Batail, Anissa Bendjeriou, Laurent Djakovitch^*, Véronique Dufaud

^*Corresponding author for this work

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

31 Scopus citations

Abstract

Heterogeneous palladium catalysts were prepared by covalent immobilization of palladium (II) complexes of the general formula PdCl₂L₂ (L = P, CN) onto SBA-15 silica using a post-synthetic method. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. In general, all the palladium modified solids exhibited highly ordered mesostructures while keeping the integrity of the parent molecular precursors. The catalytic performances of the materials were evaluated in the heteroannulation of 2-iodoaniline and 2-bromoaniline with triethyl(phenylethynyl)silane which showed high activities and selectivities with isolated yields in the range of 80-85%. Despite a decrease in the initial activity, quantitative conversion of iodoaniline to the expected product was observed over multiple recyclings, making these materials particularly efficient for such applications. The catalytic process was shown to be homogeneous in nature, the solid apparently serving as a "reservoir" for the metal between cycles.

Original language	English (US)
Pages (from-to)	179-187
Number of pages	9
Journal	Applied Catalysis A: General
Volume	388
Issue number	1-2
DOIs	https://doi.org/10.1016/j.apcata.2010.08.046
State	Published - Nov 20 2010
Externally published	Yes

Bibliographical note

Funding Information:
The authors gratefully acknowledge the Région Rhône-Alpes Programme CIBLE-2007 (Contract number 07 016376 01/02/03) and the National Agency of Research (No. ANR-07-BLAN-0167-01/02) for funding. NB thanks Région Rhône-Alpes for a grant. AB thanks ANR for felowship. The authors kindly acknowledge the “Technical Center” of IRCELYON for analyses and helpful discussions (M. Aouine and L. Burel for TEM, P. Mascunan and N. Cristin for AAS analyses, P. Delichère and S. Prakash for XPS, F. Bosselet and G. Bergeret for XRD and C. Lorentz for solid-state NMR).

Keywords

Heterogenous catalysis
Indoles
Larock synthesis
Palladium catalysts
SBA-15

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology

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10.1016/j.apcata.2010.08.046

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title = "Larock indole synthesis using palladium complexes immobilized onto mesoporous silica",

abstract = "Heterogeneous palladium catalysts were prepared by covalent immobilization of palladium (II) complexes of the general formula PdCl2L2 (L = P, CN) onto SBA-15 silica using a post-synthetic method. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. In general, all the palladium modified solids exhibited highly ordered mesostructures while keeping the integrity of the parent molecular precursors. The catalytic performances of the materials were evaluated in the heteroannulation of 2-iodoaniline and 2-bromoaniline with triethyl(phenylethynyl)silane which showed high activities and selectivities with isolated yields in the range of 80-85%. Despite a decrease in the initial activity, quantitative conversion of iodoaniline to the expected product was observed over multiple recyclings, making these materials particularly efficient for such applications. The catalytic process was shown to be homogeneous in nature, the solid apparently serving as a {"}reservoir{"} for the metal between cycles.",

keywords = "Heterogenous catalysis, Indoles, Larock synthesis, Palladium catalysts, SBA-15",

author = "Nelly Batail and Anissa Bendjeriou and Laurent Djakovitch and V{\'e}ronique Dufaud",

note = "Funding Information: The authors gratefully acknowledge the R{\'e}gion Rh{\^o}ne-Alpes Programme CIBLE-2007 (Contract number 07 016376 01/02/03) and the National Agency of Research (No. ANR-07-BLAN-0167-01/02) for funding. NB thanks R{\'e}gion Rh{\^o}ne-Alpes for a grant. AB thanks ANR for felowship. The authors kindly acknowledge the “Technical Center” of IRCELYON for analyses and helpful discussions (M. Aouine and L. Burel for TEM, P. Mascunan and N. Cristin for AAS analyses, P. Delich{\`e}re and S. Prakash for XPS, F. Bosselet and G. Bergeret for XRD and C. Lorentz for solid-state NMR). ",

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AU - Batail, Nelly

AU - Bendjeriou, Anissa

AU - Djakovitch, Laurent

AU - Dufaud, Véronique

N1 - Funding Information: The authors gratefully acknowledge the Région Rhône-Alpes Programme CIBLE-2007 (Contract number 07 016376 01/02/03) and the National Agency of Research (No. ANR-07-BLAN-0167-01/02) for funding. NB thanks Région Rhône-Alpes for a grant. AB thanks ANR for felowship. The authors kindly acknowledge the “Technical Center” of IRCELYON for analyses and helpful discussions (M. Aouine and L. Burel for TEM, P. Mascunan and N. Cristin for AAS analyses, P. Delichère and S. Prakash for XPS, F. Bosselet and G. Bergeret for XRD and C. Lorentz for solid-state NMR).

PY - 2010/11/20

Y1 - 2010/11/20

N2 - Heterogeneous palladium catalysts were prepared by covalent immobilization of palladium (II) complexes of the general formula PdCl2L2 (L = P, CN) onto SBA-15 silica using a post-synthetic method. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. In general, all the palladium modified solids exhibited highly ordered mesostructures while keeping the integrity of the parent molecular precursors. The catalytic performances of the materials were evaluated in the heteroannulation of 2-iodoaniline and 2-bromoaniline with triethyl(phenylethynyl)silane which showed high activities and selectivities with isolated yields in the range of 80-85%. Despite a decrease in the initial activity, quantitative conversion of iodoaniline to the expected product was observed over multiple recyclings, making these materials particularly efficient for such applications. The catalytic process was shown to be homogeneous in nature, the solid apparently serving as a "reservoir" for the metal between cycles.

AB - Heterogeneous palladium catalysts were prepared by covalent immobilization of palladium (II) complexes of the general formula PdCl2L2 (L = P, CN) onto SBA-15 silica using a post-synthetic method. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. In general, all the palladium modified solids exhibited highly ordered mesostructures while keeping the integrity of the parent molecular precursors. The catalytic performances of the materials were evaluated in the heteroannulation of 2-iodoaniline and 2-bromoaniline with triethyl(phenylethynyl)silane which showed high activities and selectivities with isolated yields in the range of 80-85%. Despite a decrease in the initial activity, quantitative conversion of iodoaniline to the expected product was observed over multiple recyclings, making these materials particularly efficient for such applications. The catalytic process was shown to be homogeneous in nature, the solid apparently serving as a "reservoir" for the metal between cycles.

KW - Heterogenous catalysis

KW - Indoles

KW - Larock synthesis

KW - Palladium catalysts

KW - SBA-15

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Larock indole synthesis using palladium complexes immobilized onto mesoporous silica

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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