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Flow Chemistry in Organic Synthesis
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Flow Chemistry in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 July 2020) | Viewed by 23427

Special Issue Editors

Prof. Dr. Maurizio Benaglia

E-Mail Website
Guest Editor
Dipartimento di Chimica, Università degli Studi di Milano via Golgi 19, 20133 Milano, Italy
Interests: stereoselective synthesis; sustainable methodologies and their application to the synthesis of chiral products of pharmaceutical interest; design and development of chiral organocatalysts; stereoselective reactions in water and other alternative reaction mediums; supported-catalysts and catalytic reactors; enantioselective transformations under continuous-flow conditions; 3D-printing technologies for micro- and mesoreactors
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Miquel A. Pericàs

E-Mail Website
Guest Editor
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Tarragona, Spain
Interests: asymmetric catalysis; immobilized catalysts; flow chemistry; ligand and catalyst design; photocatalysis; click chemistry; magnetic nanoparticles

Special Issue Information

Dear Colleagues,

In the last years, organic synthesis has been greatly influenced by the widespread diffusion of continuous flow technologies, which have revolutionized not only the synthesis and manufacturing of chemical products but also the design and development of novel reactions.

The present Special Issue “Flow Chemistry in Organic Synthesis” aims to collect and disseminate some of the most significant and recent contributions in the very wide and highly interdisciplinary area of continuous flow organic reactions.

The scope is broad and includes, among others, the use of micro- and mesofludic devices, flow and catalytic reactors, the application of innovative heating techniques, 3D-printing, photochemical reactions under continuous flow conditions, catalytic and enzymatic transformations, and the development of in-flow reactions in alternative solvents (ionic liquids and deep eutectic solvents). A special focus will be given to the synthesis of chiral molecules, building blocks, or intermediates for the preparation of industrial products, active pharmaceutical ingredients, and biologically active compounds.

Prof. Dr. Maurizio Benaglia
Prof. Miquel A. Pericàs
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Flow reactors
  • Catalytic reactors
  • 3D-printing
  • Enzymatic reactions
  • Deep eutectic solvents
  • Photochemistry
  • Microreactors

Published Papers (5 papers)

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Research

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10 pages, 2820 KiB  
Article
Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan
by Margherita Pirola, Alessandra Puglisi, Laura Raimondi, Alessandra Forni and Maurizio Benaglia
Molecules 2019, 24(12), 2260; https://doi.org/10.3390/molecules24122260 - 18 Jun 2019
Cited by 6 | Viewed by 2925
Abstract
A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the [...] Read more.
A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the catalytic reduction of a fluorinated enamine with trichlorosilane as reducing agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation of the target chiral fluorinated amine in up to an 87:13 diastereoisomeric ratio. Full article
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
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9 pages, 4040 KiB  
Article
Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
by Reinout Van Kerrebroeck, Pieter Naert, Thomas S. A. Heugebaert, Matthias D’hooghe and Christian V. Stevens
Molecules 2019, 24(11), 2116; https://doi.org/10.3390/molecules24112116 - 04 Jun 2019
Cited by 16 | Viewed by 5897
Abstract
Bromination reactions are crucial in today’s chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br2) makes these brominations very challenging and [...] Read more.
Bromination reactions are crucial in today’s chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br2) makes these brominations very challenging and hazardous. We describe here a safe and straightforward protocol for bromination in continuous flow. The hazardous Br2 or KOBr is generated in situ by reacting an oxidant (NaOCl) with HBr or KBr, respectively, which is directly coupled to the bromination reaction and a quench of residual bromine. This protocol was demonstrated by polybrominating both alkenes and aromatic substrates in a wide variety of solvents, with yields ranging from 78% to 99%. The protocol can easily be adapted for the bromination of other substrates in an academic and industrial environment. Full article
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
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18 pages, 3253 KiB  
Article
Flow Hydrodediazoniation of Aromatic Heterocycles
by Liesa Röder, Alexander J. Nicholls and Ian R. Baxendale
Molecules 2019, 24(10), 1996; https://doi.org/10.3390/molecules24101996 - 24 May 2019
Cited by 11 | Viewed by 5055
Abstract
Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process [...] Read more.
Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system. Full article
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
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8 pages, 2455 KiB  
Article
Metal-Free Alpha Trifluoromethylselenolation of Carbonyl Derivatives under Batch and Flow Conditions
by Elisabetta Massolo, Margherita Pirola, Sergio Rossi and Tiziana Benincori
Molecules 2019, 24(4), 726; https://doi.org/10.3390/molecules24040726 - 18 Feb 2019
Cited by 9 | Viewed by 2775
Abstract
Trifluoromethylselenolated carbonyl compounds represent an emerging class with potential applications in several fields; however, a widespread use of such compound is hampered by the very limited number of strategies for their preparation. In this study we developed a method for the preparation of [...] Read more.
Trifluoromethylselenolated carbonyl compounds represent an emerging class with potential applications in several fields; however, a widespread use of such compound is hampered by the very limited number of strategies for their preparation. In this study we developed a method for the preparation of α-SeCF3 substituted carbonyl derivatives using an in situ generated electrophilic ClSeCF3 species. We also implemented an in-flow protocol to improve the safety features of the process. Full article
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
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Review

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19 pages, 8162 KiB  
Review
Anionic Polymerization Using Flow Microreactors
by Yusuke Takahashi and Aiichiro Nagaki
Molecules 2019, 24(8), 1532; https://doi.org/10.3390/molecules24081532 - 18 Apr 2019
Cited by 17 | Viewed by 5678
Abstract
Flow microreactors are expected to make a revolutionary change in chemical synthesis involving various fields of polymer synthesis. In fact, extensive flow microreactor studies have opened up new possibilities in polymer chemistry including cationic polymerization, anionic polymerization, radical polymerization, coordination polymerization, polycondensation and [...] Read more.
Flow microreactors are expected to make a revolutionary change in chemical synthesis involving various fields of polymer synthesis. In fact, extensive flow microreactor studies have opened up new possibilities in polymer chemistry including cationic polymerization, anionic polymerization, radical polymerization, coordination polymerization, polycondensation and ring-opening polymerization. This review provides an overview of flow microreactors in anionic polymerization and their various applications. Full article
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
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