Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Palo‐Nieto, Carlos; Afewerki, Samson; Anderson, Mattias; Tai, Cheuk‐Wai; Berglund, Per; Córdova, Armando

doi:10.1021/acscatal.6b01031

Cited by 47 publications

(40 citation statements)

References 75 publications

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“…Córdova and co-workers disclosed asymmetric one-pot heterogeneous metal -enzymatic relay catalytic processes using Pd NPs anchored on aminopropyl-functionalized mesocellular silica foam catalyst developed previously (Pd NPs/ support, 97 Scheme 3). 223 Aromatic ketones 180 were transformed into racemic amines 181 by reductive amination using HCOONH 4 for the in situ generation of imines and also the hydrogen source in the reductive step catalysed by Pd. The enzymatic KR of the racemic amines followed this heterogeneous catalytic step by transformation of 181 into amides 182 using lipase (CALB, Novozym-435) catalyst and ethyl methoxyacetate as acylation agent.…”

Section: View Article Onlinementioning

confidence: 99%

“…223 Palladium NPs stabilized by thermostable protein (Pd NPs/Te-Dps; Dps: DNA binding protein from starved cells) was used in the one-pot sequential Suzuki-Miyaura crosscoupling and enzymatic enantioselective reduction of phenylboronic acid 39 and phenyl iodide 183 derivatives, with one of the substrates bearing the acetyl group in the para position. The acetyl biaryl intermediates 184 were reduced to chiral biaryl alcohols 40.…”

Section: View Article Onlinementioning

confidence: 99%

“…223 Scheme 52 Sequential one-pot Suzuki-Miyaura reaction followed by enzymatic enantioselective reduction (a) and stereoselective epoxidation followed by asymmetric enzymatic hydrolysis (b). View Article Online types concomitantly, due to often met incompatibilities with the components needed in different steps.…”

Section: View Article Onlinementioning

confidence: 99%

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Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

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The preparation of optically pure fine chemicals is among the most important and challenging tasks met by organic chemists. Recently, significant efforts have been focused on the development of green and sustainable procedures for the synthesis of these high value-added compounds. Asymmetric heterogeneous catalysis has provided efficient solutions to these challenges. The application of heterogeneous chiral catalysts in one-pot processes combines the advantages of use of these materials with time, material, and energy savings associated with cascade or sequential procedures. This review surveys these asymmetric onepot reactions reported until July 2017, in which a heterogeneous chemical catalyst has been applied either as a single multifunctional catalyst or in combination with a second catalytically active material. These processes include one-pot procedures catalysed by carefully designed solids obtained by the immobilization of chiral metal complexes, by anchoring chiral organocatalysts, or by modifying catalytic surfaces with optically pure compounds, which may also incorporate uncatalyzed and homogeneously catalysed steps. Methods applying achiral heterogeneous catalysts in combination with soluble chiral chemical catalysts or biocatalysts are also presented. Sophisticated, finely tuned materials have been applied in most of these reactions, which have been discussed along with the main requirements necessary to perform these transformations in a one-pot manner.

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Section: View Article Onlinementioning

confidence: 99%

Section: View Article Onlinementioning

confidence: 99%

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Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

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“…Most recently, Berglund and co-workers integrated heterogeneous Pd(0)-aminopropyl-mesocellular foam (Pd(0)-AmP-MCF) or Pd(0)-aminopropyl-conrolled pore glass (Pd(0)-AmP-CPG) and CALB catalysts in one-pot for eco-friendly and asymmetric synthesis of valuable molecules such as amines and amides from an aldehyde, ketone or an alcohol respectively in good to high overall yields [50]. In this work, they developed several novel cocatalytic relay sequences, including reductive amination/amidation (Scheme 5A), aerobic oxidation/reductive amination/amidation (Scheme 5B), and reductive amination/dynamic kinetic resolution (Scheme 5C).…”

Section: Other Tandem Reactions By Transition Metal Catalysts and Lipmentioning

confidence: 99%

Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis

Wang

Zhao

2016

Catalysts

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Abstract:The application of biocatalysts in the synthesis of fine chemicals and medicinal compounds has grown significantly in recent years. Particularly, there is a growing interest in the development of one-pot tandem catalytic systems combining the reactivity of a chemical catalyst with the selectivity engendered by the active site of an enzyme. Such tandem catalytic systems can achieve levels of chemo-, regio-, and stereo-selectivities that are unattainable with a small molecule catalyst. In addition, artificial metalloenzymes widen the range of reactivities and catalyzed reactions that are potentially employable. This review highlights some of the recent examples in the past three years that combined transition metal catalysis with enzymatic catalysis. This field is still in its infancy. However, with recent advances in protein engineering, catalyst synthesis, artificial metalloenzymes and supramolecular assembly, there is great potential to develop more sophisticated tandem chemoenzymatic processes for the synthesis of structurally complex chemicals.

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“…All of these features characterize a sustainable and eco-friendly technology. Based on the above challenges and our previous experience in developing palladium based heterogenous catalysts for various green chemical transformations [23][24][25][26][27][28][29] , we designed an eco-friendly approach for the preparation of heterogeneous and multifunctional palladium catalysts suitable for a wide spectrum of chemical transformations. The activity and versatility of the designed catalysts was demonstrated in the Suzuki-Miyaura cross-coupling reaction, aerobic oxidation approach of allylic alcohols and stereoselective cascade carbocyclization reactions (Fig.…”

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confidence: 99%

Sustainable and recyclable heterogenous palladium catalysts from rice husk-derived biosilicates for Suzuki-Miyaura cross-couplings, aerobic oxidations and stereoselective cascade carbocyclizations

Afewerki

Franco

Balu

et al. 2020

Sci Rep

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A new eco-friendly approach for the preparation of sustainable heterogeneous palladium catalysts from rice husk-derived biogenic silica (RH p-Si and RH U-Si). the designed heterogeneously supported palladium species (RH p-Si-nH 2-pd and RH U-Si-nH 2-pd) were fully characterized and successfully employed as catalysts for various chemical transformations (c-c bond-forming reactions, aerobic oxidations and carbocyclizations). Suzuki-Miyaura transformations were highly efficient in a green solvent system (H 2 O:EtOH (1:1) with excellent recyclability, providing the cross-coupling products with a wide range of functionalities in high isolated yields (up to 99%). Palladium species (Pd(0)nanoparticles or Pd(II)) were also efficient catalysts in the green aerobic oxidation of an allylic alcohol and a co-catalytic stereoselective cascade carbocyclization transformation. in the latter case, a quaternary stereocenter was formed with excellent stereoselectivity (up to 27:1 dr). Rice husk (RH) is a major waste product from the rice industry with high content of silica. This abundant material is a sustainable and cheap raw material and therefore within the context of sustainability 1. De facto, rice husk ash (RHA) is known to contain 94% silica 2. Here, silica is a very important component for various industrial and biomedical applications 3 , being high surface area silicates highly desirable and good candidates as catalyst support 4. For these reasons the development of efficient methods for the preparation of silica and silica based materials are of high interest. In general, the production of silica from RH is energy intensive i.e. obtained by burning RH in a muffle furnace at high temperature (500, 600 or 700 °C) 5,6. Nevertheless, even though there are some reports on simple and energy-efficient method for the generation of silica from RH, drawbacks such as risk for mineral contamination 7 , several acid and based extraction steps or tedious approaches 8 are encountered 9. In this context, novel methods for the extraction of silica in an eco-friendly, cost-efficient, scalable and facile approach can be highly attractive. This report discloses the preparation of palladium based multifunctional heterogenous catalysts from RH-derived silica as support. There are reports on the immobilization of various metals on RH and their use as heterogeneous catalysts for chemical syntheses 10-16. In this context, Chang and co-workers

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Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Cited by 47 publications

References 75 publications

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis

Sustainable and recyclable heterogenous palladium catalysts from rice husk-derived biosilicates for Suzuki-Miyaura cross-couplings, aerobic oxidations and stereoselective cascade carbocyclizations

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