Abstract
We report on the synthesis and catalytic properties of a class of hybrid organic-inorganic mesoporous bifunctional heterogeneous catalysts for efficient catalysis of two-step tandem reactions in one pot. With a solvent-assisted grafting method, two different catalytic groups, that is, an organoamine and a palladium-organodiamine complex, were immobilized onto high-surface-area mesoporous silica sequentially, by using their corresponding organosilanes in 2-propanol or toluene as the solvent in the first step and toluene as the solvent in the second step. Both MCM-41 and SBA-15 mesoporous silicas were used as support materials for the two catalytic groups, and the effect of different sequential grafting of the two organosilanes in 2-propanol or toluene on the structures and the catalytic properties of the resulting bifunctional catalysts were investigated. By using the resulting amine/PdII-diamine bifunctional mesoporous material as catalyst, the occurrence of two very important C-C bond forming reactions, that is, the Sonogashira and the Henry reactions, was demonstrated in one pot for the first time. Yields of approximately 100 % in 2.5 h for the Sonogashira reaction and approximately 100 % in 45 min for the Henry reaction were obtained in the presence of the bifunctional catalyst when the reactions were run individually. When the bifunctional catalyst was used to catalyze the Sonogashira-Henry reactions in tandem in one pot, a yield of up to approximately 60 % of the Sonogashira-Henry product in 5 h was obtained. The synthesis and use of such bifunctional catalysts for efficient catalysis of the tandem reaction is of importance in three significant ways: it prevents the unnecessary use of solvents and other chemicals required for the purification of the intermediate products of either individual reaction, eliminates some of the work-up procedures, and lowers the cost of synthesis of the final product.
| Original language | English |
|---|---|
| Pages (from-to) | 3174-3182 |
| Number of pages | 9 |
| Journal | European Journal of Inorganic Chemistry |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - Jul 2011 |
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Keywords
- Bifunctional catalysts
- C-C coupling
- Heterogeneous catalysis
- Mesoporous materials
- Palladium
ASJC Scopus subject areas
- Inorganic Chemistry
Cite this
Bifunctional mesoporous silica catalyst for C-C bond forming tandem reactions. / Sharma, Krishna K.; Biradar, Ankush V.; Das, Sayantani; Asefa, Teddy.
In: European Journal of Inorganic Chemistry, No. 21, 07.2011, p. 3174-3182.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Bifunctional mesoporous silica catalyst for C-C bond forming tandem reactions
AU - Sharma, Krishna K.
AU - Biradar, Ankush V.
AU - Das, Sayantani
AU - Asefa, Teddy
PY - 2011/7
Y1 - 2011/7
N2 - We report on the synthesis and catalytic properties of a class of hybrid organic-inorganic mesoporous bifunctional heterogeneous catalysts for efficient catalysis of two-step tandem reactions in one pot. With a solvent-assisted grafting method, two different catalytic groups, that is, an organoamine and a palladium-organodiamine complex, were immobilized onto high-surface-area mesoporous silica sequentially, by using their corresponding organosilanes in 2-propanol or toluene as the solvent in the first step and toluene as the solvent in the second step. Both MCM-41 and SBA-15 mesoporous silicas were used as support materials for the two catalytic groups, and the effect of different sequential grafting of the two organosilanes in 2-propanol or toluene on the structures and the catalytic properties of the resulting bifunctional catalysts were investigated. By using the resulting amine/PdII-diamine bifunctional mesoporous material as catalyst, the occurrence of two very important C-C bond forming reactions, that is, the Sonogashira and the Henry reactions, was demonstrated in one pot for the first time. Yields of approximately 100 % in 2.5 h for the Sonogashira reaction and approximately 100 % in 45 min for the Henry reaction were obtained in the presence of the bifunctional catalyst when the reactions were run individually. When the bifunctional catalyst was used to catalyze the Sonogashira-Henry reactions in tandem in one pot, a yield of up to approximately 60 % of the Sonogashira-Henry product in 5 h was obtained. The synthesis and use of such bifunctional catalysts for efficient catalysis of the tandem reaction is of importance in three significant ways: it prevents the unnecessary use of solvents and other chemicals required for the purification of the intermediate products of either individual reaction, eliminates some of the work-up procedures, and lowers the cost of synthesis of the final product.
AB - We report on the synthesis and catalytic properties of a class of hybrid organic-inorganic mesoporous bifunctional heterogeneous catalysts for efficient catalysis of two-step tandem reactions in one pot. With a solvent-assisted grafting method, two different catalytic groups, that is, an organoamine and a palladium-organodiamine complex, were immobilized onto high-surface-area mesoporous silica sequentially, by using their corresponding organosilanes in 2-propanol or toluene as the solvent in the first step and toluene as the solvent in the second step. Both MCM-41 and SBA-15 mesoporous silicas were used as support materials for the two catalytic groups, and the effect of different sequential grafting of the two organosilanes in 2-propanol or toluene on the structures and the catalytic properties of the resulting bifunctional catalysts were investigated. By using the resulting amine/PdII-diamine bifunctional mesoporous material as catalyst, the occurrence of two very important C-C bond forming reactions, that is, the Sonogashira and the Henry reactions, was demonstrated in one pot for the first time. Yields of approximately 100 % in 2.5 h for the Sonogashira reaction and approximately 100 % in 45 min for the Henry reaction were obtained in the presence of the bifunctional catalyst when the reactions were run individually. When the bifunctional catalyst was used to catalyze the Sonogashira-Henry reactions in tandem in one pot, a yield of up to approximately 60 % of the Sonogashira-Henry product in 5 h was obtained. The synthesis and use of such bifunctional catalysts for efficient catalysis of the tandem reaction is of importance in three significant ways: it prevents the unnecessary use of solvents and other chemicals required for the purification of the intermediate products of either individual reaction, eliminates some of the work-up procedures, and lowers the cost of synthesis of the final product.
KW - Bifunctional catalysts
KW - C-C coupling
KW - Heterogeneous catalysis
KW - Mesoporous materials
KW - Palladium
UR - http://www.scopus.com/inward/record.url?scp=79960239501&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79960239501&partnerID=8YFLogxK
U2 - 10.1002/ejic.201001332
DO - 10.1002/ejic.201001332
M3 - Article
AN - SCOPUS:79960239501
SP - 3174
EP - 3182
JO - Chemische Berichte
JF - Chemische Berichte
SN - 0009-2940
IS - 21
ER -