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Current State of Microflow Trifluoromethylation Reactions.
Chem Rec
September 2023
Department of Engineering, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya, 466-8555, Japan.
The trifluoromethyl group is a powerful structural motif in drugs and polymers; thus, developing trifluoromethylation reactions is an important area of research in organic chemistry. Over the past few decades, significant progress has been made in developing new methods for the trifluoromethylation of organic molecules, ranging from nucleophilic and electrophilic approaches to transition-metal catalysis, photocatalysis, and electrolytic reactions. While these reactions were initially developed in batch systems, more recent microflow versions are highly attractive for industrial applications owing to their scalability, safety, and time efficiency.
View Article and Find Full Text PDFIn-line Multidimensional NMR Monitoring of Photochemical Flow Reactions.
Chemistry
April 2023
Nantes Université, CNRS, CEISAM UMR6230, F-4400, Nantes, France.
This work demonstrates the in-line monitoring of a flow photochemical reaction using 1D and ultrafast 2D NMR methods at high magnetic field. The reaction mixture exiting the flow reactor is flown through the NMR spectrometer and directly analyzed. In the case of simple substrates, suitable information can be obtained through 1D H spectra, but for molecules of higher complexity the use of 2D experiments is key to address signal overlaps and assignment issues.
View Article and Find Full Text PDFFlow Photochemistry for Single-Chain Polymer Nanoparticle Synthesis.
Angew Chem Int Ed Engl
January 2021
Schulich Faculty of Chemistry and The Interdepartmental Program in Polymer Engineering, Technion-Israel Institute of Technology, Haifa, 3200003, Israel.
Single chain polymer nanoparticles (SCNP) are an attractive polymer architecture that provides functions seen in folded biomacromolecules. The generation of SCNPs, however, is limited by the requirement of a high dilution chemical step, necessitating the use of large reactors to produce processable quantities of material. Herein, the chemical folding of macromolecules into SCNPs is achieved in both batch and flow photochemical processes by the previously described photodimerization of anthracene units in polymethylmethacrylate (100 kDa) under UV irradiation at 366 nm.
View Article and Find Full Text PDFA rapid and clean synthetic approach to cyclic peptides via micro-flow peptide chain elongation and photochemical cyclization: synthesis of a cyclic RGD peptide.
Org Biomol Chem
November 2016
Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
A cyclic RGD peptide was efficiently synthesized based on micro-flow, triphosgene-mediated peptide chain elongation and micro-flow photochemical macrolactamization. Our approach enabled a rapid (amidation for peptide chain elongation <5 s, macrolactamization <5 min) and clean (only one column chromatographic separation) synthesis of a cyclic peptide.
View Article and Find Full Text PDFAccelerated gas-liquid visible light photoredox catalysis with continuous-flow photochemical microreactors.
Nat Protoc
January 2016
Eindhoven University of Technology, Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven, the Netherlands.
In this protocol, we describe the construction and use of an operationally simple photochemical microreactor for gas-liquid photoredox catalysis using visible light. The general procedure includes details on how to set up the microreactor appropriately with inlets for gaseous reagents and organic starting materials, and it includes examples of how to use it to achieve continuous-flow preparation of disulfides or trifluoromethylated heterocycles and thiols. The reported photomicroreactors are modular, inexpensive and can be prepared rapidly from commercially available parts within 1 h even by nonspecialists.
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