Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor

Wernik, Michaela; Sipos, Gellért; Buchholcz, Balázs; Darvas, Ferenç; Novàk, Zoltán; Ötvös, Sándor B.; Kappe, C. Oliver

doi:10.1039/d1gc02039k

Cited by 24 publications

(15 citation statements)

References 62 publications

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“…One case in point, as depicted in Figure , has started to appear in the literature, and while not yet having fully merged bio- and chemo-catalysis, the next steps are surely coming, while the impact along these lines is already clear. Additional technological developments are also worthy of note, including the use of hydrophobic effects and polymer-induced kinetic effects of hydroxypropyl methylcellulose (HPMC) in water. − Photocatalysis , and the use of flow chemistry in water − have also paved the way for very exciting future developments that will very likely be brought to fruition in the near-term.…”

Section: Discussionmentioning

confidence: 99%

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Where Chemocatalysis Meets Biocatalysis: In Water

2022

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Chemoenzymatic catalysis, by definition, involves the merging of sequential reactions using both chemocatalysis and biocatalysis, typically in a single reaction vessel. A major challenge, the solution to which, however, is associated with numerous advantages, is to run such one-pot processes in water: the majority of enzyme-catalyzed processes take place in water as Nature’s reaction medium, thus enabling a broad synthetic diversity when using water due to the option to use virtually all types of enzymes. Furthermore, water is cheap, abundantly available, and environmentally friendly, thus making it, in principle, an ideal reaction medium. On the other hand, most chemocatalysis is routinely performed today in organic solvents (which might deactivate enzymes), thus appearing to make it difficult to combine such reactions with biocatalysis toward one-pot cascades in water. Several creative approaches and solutions that enable such combinations of chemo- and biocatalysis in water to be realized and applied to synthetic problems are presented herein, reflecting the state-of-the-art in this blossoming field. Coverage has been sectioned into three parts, after introductory remarks: (1) Chapter 2 focuses on historical developments that initiated this area of research; (2) Chapter 3 describes key developments post-initial discoveries that have advanced this field; and (3) Chapter 4 highlights the latest achievements that provide attractive solutions to the main question of compatibility between biocatalysis (used predominantly in aqueous media) and chemocatalysis (that remains predominantly performed in organic solvents), both Chapters covering mainly literature from ca. 2018 to the present. Chapters 5 and 6 provide a brief overview as to where the field stands, the challenges that lie ahead, and ultimately, the prognosis looking toward the future of chemoenzymatic catalysis in organic synthesis.

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Section: Discussionmentioning

confidence: 99%

“…This potential mismatch can obviously be addressed via enzyme engineering to boost throughput of the biotransformation. 132 technology and sufficient time to solve the problem, with the risk that the outcome may not be fruitful.…”

Section: Challenges and Limitationsmentioning

confidence: 99%

Where Chemocatalysis Meets Biocatalysis: In Water

2022

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“…Downstream mixing is typically achieved through serpentine bends imparting Dean vortices in microreactors or static mixers, e.g., Kenics or SMX, 48 in millireactors. Oscillatory flow either through baffles 49 or combined with static mixing elements 50 can also help impart high intensity mixing, whereas Taylor or segmented flow generates plug flow (essentially creating microbatch reactors) with varied mixing intensity dependent on tubing/channel size. 51,52 Next, the question is how to impart the required energy for the process into the system.…”

Section: ■ Taking a Process Into Flowmentioning

confidence: 99%

Quid Pro Flow

2023

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How do you get into flow? We trained in flow chemistry during postdoctoral research and are now applying it in new areas: materials chemistry, crystallization, and supramolecular synthesis. Typically, when researchers think of "flow", they are considering predominantly liquid-based organic synthesis; application to other disciplines comes with its own challenges. In this Perspective, we highlight why we use and champion flow technologies in our fields, summarize some of the questions we encounter when discussing entry into flow research, and suggest steps to make the transition into the field, emphasizing that communication and collaboration between disciplines is key.

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“…, slurries, viscous solutions). 29–32 Polymerizations typically lead to increasing viscosities, which also challenges the integrity of mixing profiles. The novel OFR described in this work ( i.e.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, a scalable oscillatory flow reactor (OFR) with a planar reaction compartment (15 mL internal capacity) has been used to successfully conduct organic small molecule transformations when processing challenging media (e.g., slurries, viscous solutions). [29][30][31][32] Polymerizations typically lead to increasing viscosities, which also challenges the integrity of mixing profiles. The novel OFR described in this work (i.e.…”

Section: Introductionmentioning

confidence: 99%