Silica‐Supported Molecular Catalysts for Tandem Reactions

Jin, Ronghua; Zheng, Dongsong; Li, Rui; Li, Guohua

doi:10.1002/cctc.201701718

Cited by 43 publications

(33 citation statements)

References 153 publications

(236 reference statements)

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“…Heterogeneous acid-base bi-functional catalysts have been reported to promote asymmetric reactions successfully with good activity and high enantioselectivity [34], which could well solve the tough problem of mutual deactivation [35] of acid and base sites in homogeneous counterparts. Immobilized acid and base active sites could supply efficient synergistic catalysis as previously reported [36][37][38][39][40][41]. Our group more recently reported efficient synergistic catalysis achieved with inherent achiral silanols of mesoporous silica as acidic sites and immobilized chiral amines as basic sites in the direct asymmetric aldol condensation [42], the asymmetric Henry-Michael one-pot reaction [43], oxa-Michael-Michael cascade reaction [44] and Knoevenagel-phospha-Michael tandem reaction [45].…”

Section: Introductionmentioning

confidence: 73%

Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline

Chen

Jiang

et al. 2019

Catalysts

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Heterogeneous synergistic catalysis by SBA-15 immobilized chiral amines catalysts has promoted efficient aza-Michael–Henry tandem reaction for the synthesis of chiral 3-Nitro-1,2-Dihydroquinoline. Final products in the asymmetric aza-Michael–Henry cascade reactions between 2-aminobenzaldehyde and β-nitrostyrolene were afforded in a yield of 85% and an enantiomeric excess (ee) value of 98% on (S)-(–)-2-aminomethyl-1-ethylpyrrolidine immobilized SBA-15. SBA-15-AEP catalyst has been also extended to the asymmetric aza-Michael–Henry cascade reaction of substituted R1-2-aminobenzaldehyde and R2-substituted nitroolefin. The heterogeneous synergistic mechanism for both tertiary amine and secondary amine immobilized mesoporous has been proposed in detail including the geometrical constraints in the ee promotion.

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Section: Introductionmentioning

confidence: 73%

Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline

Chen

Jiang

et al. 2019

Catalysts

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“…In our previous work, synergic catalysis was achieved with inherent achiral silanols of mesoporous silica as acidic sites and immobilized chiral amines as basic sites, affording satisfactory yield and ee in the direct asymmetric aldol condensation, the asymmetric Henry‐Michael one‐pot reaction and oxa‐Michael‐Michael cascade reaction . Recently, some heterogeneous catalysts based on the mesoporous materials immobilized metal complex has also been reported to catalyze the tandem reaction …”

Section: Introductionmentioning

confidence: 98%

Asymmetric Knoevenagel‐Phospha‐Michael Tandem Reaction Synergistically Catalyzed by Achiral Silanols and Grafted Chiral Amines on Mesoporous Silica

Yan

Jiang

et al. 2019

Asian J Org Chem

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Highly efficient and enantioselective asymmetric Knoevenagel-phospha-Michael tandem reactions have been achieved on bifunctional heterogeneous catalysts with inherent silanols as acidic sites and immobilized chiral amines as basic sites. Final products were afforded in yields of up to 99% and ee values of up to 99%. The effects of substituents on benzaldehyde and molecular dimensions of phosphites have also been investigated. Larger substrates can access the catalytic site inside larger mesoporous pores, thereby improving both of yield and ee of final products.

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“…Nevertheless, direct use of metallic nanoparticles suffers from some demerits in catalyst activity, stability and separation due to their aggregative nature. Immobilization of the metals on the support is a pivotal way to overcome these mentioned problems …”

Section: Introductionmentioning

confidence: 99%

Introduction of Ag/CuO/MCM‐48 as an efficient catalyst for the one‐pot synthesis of novel pyran‐pyrrole hybrids

Tavakoli

Mamaghani

Sheykhan

2019

Applied Organom Chemis

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Bimetallic silver and copper incorporated mesoporous MCM‐48 (Ag/CuO/MCM‐48) was synthesized by simple wet‐impregnation method. The knowledge about its structural properties was gathered by means of Fourier transform‐infrared, energy‐dispersive X‐ray, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy and Brunauer–Emmett–Teller analyses. The catalytic activity of Ag/CuO/MCM‐48 was examined in the one‐pot three‐component reaction of 3‐(1‐methyl‐1H‐pyrrol‐2‐yl)‐3‐oxopropanenitrile, malononitrile and various aromatic aldehydes leading to novel pyran‐pyrrole hybrid derivatives in reduced reaction times (5–10 min) and excellent yields (88–97%). Application of Ag/CuO/MCM‐48 as a potent heterogeneous catalyst with good reusability up to five times, use of ethanol as an eco‐compatible medium and chromatography‐free work‐up are some crucial green aspects of this procedure.

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Silica‐Supported Molecular Catalysts for Tandem Reactions

Cited by 43 publications

References 153 publications

Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline

Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline

Asymmetric Knoevenagel‐Phospha‐Michael Tandem Reaction Synergistically Catalyzed by Achiral Silanols and Grafted Chiral Amines on Mesoporous Silica

Introduction of Ag/CuO/MCM‐48 as an efficient catalyst for the one‐pot synthesis of novel pyran‐pyrrole hybrids

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