Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature

Borchert, Sonja; Burda, Edyta; Schatz, J.; Hummel, Werner; Gröger, Harald

doi:10.1016/j.molcatb.2012.03.006

Cited by 56 publications

(41 citation statements)

References 19 publications

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“…In recent years, Pd‐catalyzed cross‐coupling reactions have emerged as an outstanding methodology for the formation of C−C bonds, especially for large scaffolds. Gröger and co‐workers have already shown the combination of Pd‐catalyzed cross‐coupling reactions with the enzymatic asymmetric reduction of ketones …”

Section: Introductionmentioning

confidence: 99%

Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki–Miyaura Cross‐Coupling Reactions

et al. 2016

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The combination of the biocatalytic halogenation of l‐tryptophan with subsequent chemocatalytic Suzuki–Miyaura cross‐coupling reactions leads to the modular synthesis of an array of C5, C6, or C7 aryl‐substituted tryptophan derivatives. In a three‐step one‐pot reaction, the bromo substituent is initially incorporated regioselectively by immobilized tryptophan 5‐, 6‐, or 7‐halogenases, respectively, with concomitant cofactor regeneration. The halogenation proceeds in aqueous media at room temperature in the presence of NaBr and O2. After the separation of the biocatalyst by filtration, a Pd catalyst, base, and boronic acid are added to the aryl halide formed in situ to effect direct Suzuki–Miyaura cross‐coupling reactions followed by tert‐butoxycarbonyl (Boc) protection. After a single purification step, different Boc‐protected aryl tryptophan derivatives are obtained that can, for example, be used for peptide or peptidomimetic synthesis.

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Section: Introductionmentioning

confidence: 99%

Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki–Miyaura Cross‐Coupling Reactions

et al. 2016

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“…[38] Scheme 8 Combination of a Suzuki Cross-Coupling Reaction with an Enzymatic Reduction in a Two-Step, One-Pot Process in an Aqueous Medium [37] O Ph Further exciting developments in this research area were reported by the Cacchi, Schmitzer, and Kroutil groups, demonstrating the suitability of protein-stabilized palladium nanoparticles for such transformations [39] as well as the successful use of biphasic reaction media (with an ionic liquid as the nonaqueous phase) for recycling of both the palladium and enzyme catalysts. [40] In addition, the Grçger, Hummel, and Schatz groups have recently reported the use of a palladium catalyst suitable for Suzuki reactions at room temperature in water, [41] thus enabling a perspective for the future development of a tandem-type one-pot process.…”

Section: Combination Of Palladium Catalysis With Biocatalysismentioning

confidence: 99%

3.8.2 Merging of Metal, Organic, and Enzyme Catalysis

Faber¹,

Fessner²,

Turner³

2015

Biocatalysis in Organic Synthesis 3

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Biotransformations are a valuable tool in organic synthesis, with a long-standing "track record" and an increasing tendency to be used for industrial-scale applications. [1][2][3] Whereas for many decades biocatalysis had rarely been integrated in organic synthetic reaction sequences and had long been considered more as a niche technology in organic synthesis, recently, an increased number of applications of biocatalysis in organic multistep synthesis can be seen, thus enabling alternative de novo approaches to, for example, structurally complex drug molecules, natural products, and fine chemicals. Although such biotransformations are considered to be valuable key steps, complementing the existing "classic" organic reactions as well as chemocatalytic reactions in an advantageous fashion, enzymatic reactions are still often treated as a "stand alone" reaction, which requires workup, isolation, and purification of the substrate required for the biotransformation as well as the product resulting from the biotransformation. In terms of both efficiency and sustainability it would be desirable to integrate biocatalysis more in so-called one-pot processes, which combine reactions without the need to work up intermediates. In doing so, overall solvent consumption as well as waste product formation resulting from downstreamprocessing unit operations can be dramatically decreased and space-time yield can be significantly improved. A prerequisite for such one-pot processes is compatibility of the reaction steps with each other; since enzymes (using water as the "natural solvent of choice") and chemocatalysts (running usually in an organic solvent as the typical "chemists solvent of choice") often have been considered to be poorly compatible or even incompatible, development of chemoenzymatic one-pot processes has been neglected for a long time. However, such catalytic disciplines can be combined with each other and pioneering work in this research area has already illustrated the high potential of this approach to develop more efficient multistep processes, fulfilling economic as well as sustainability requirements. Notably, enzymes as catalysts have turned out to be compatible with a broad range of man-made chemocatalysts, including heterogeneous as well as homogeneous catalysts, and metal catalysts as well as organocatalysts. This review will present an overview of major achievements in this field, noting that only a selection of them can be described herein. Earlier reviews in this field, written from different perspectives, are also available. [4][5][6][7] 3.8.2.1 Merging Metal Catalysis with BiocatalysisA major part of organic chemistry today is related to metal-catalyzed transformations, which are both highly efficient and, in many cases, highly selective. [8][9][10] Notably, in terms of their application range, metal catalysis and enzyme catalysis often complement each other. With respect to chemoenzymatic one-pot processes, combining reactions that cannot be achieved by either discipline alone is of particular inter...

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“…Bimetallic systems have become the subject of current research as they are expected to induce cooperative effects among the involved metals [3][4][5][6][7][8][9]. For the Suzuki-Miyaura/transfer hydrogenation transformation entailing C-C and C-H bond forming reactions, catalysts are mainly based on heterogeneous systems [4,10] and enzymes [11][12][13][14][15]. By contrast, homogeneous bimetallic catalysts for this tandem reaction are less common [3,5,16,17], and some of them display higher activity compared to the combination of the single monometallic species [5,17].…”

Section: Introductionmentioning

confidence: 99%

Tandem Suzuki–Miyaura/transfer hydrogenation reaction catalyzed by a Pd–Ru complex bearing an anionic dicarbene

Bitzer

Kühn

Baratta

2016

Journal of Catalysis

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Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature

Cited by 56 publications

References 19 publications

Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki–Miyaura Cross‐Coupling Reactions

Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki–Miyaura Cross‐Coupling Reactions

3.8.2 Merging of Metal, Organic, and Enzyme Catalysis

Tandem Suzuki–Miyaura/transfer hydrogenation reaction catalyzed by a Pd–Ru complex bearing an anionic dicarbene

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