Literature DB >> 32243016

Photon Equivalents as a Parameter for Scaling Photoredox Reactions in Flow: Translation of Photocatalytic C-N Cross-Coupling from Lab Scale to Multikilogram Scale.

Emily B Corcoran1, Jonathan P McMullen2, François Lévesque2, Michael K Wismer3, John R Naber2.   

Abstract

With the development of new photocatalytic methods over recent decades, the translation of these chemical reactions to industrial-production scales using continuous-flow reactors has become a topic of increasing interest. In this context, we describe our studies toward elucidating an empirically derived parameter for scaling photocatalytic reactions in flow. By evaluating the performance of a photocatalytic C-N cross-coupling reaction across multiple reactor sizes and geometries, it was demonstrated that expressing product yield as a function of the absorbed photon equivalents provides a predictive, empirical scaling parameter. Through the use of this scaling factor and characterization of the photonic flux within each reactor, the cross-coupling was scaled successfully from the milligram scale in batch to a multi-kilogram reaction in flow.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  flow chemistry; photocatalysis; photochemistry; upscaling

Year:  2020        PMID: 32243016     DOI: 10.1002/anie.201915412

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

Review 1.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

2.  Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

Authors:  David J Charboneau; Haotian Huang; Emily L Barth; Cameron C Germe; Nilay Hazari; Brandon Q Mercado; Mycah R Uehling; Susan L Zultanski
Journal:  J Am Chem Soc       Date:  2021-11-30       Impact factor: 15.419

3.  Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations.

Authors:  Zhenghui Wen; Diego Pintossi; Manuel Nuño; Timothy Noël
Journal:  Nat Commun       Date:  2022-10-18       Impact factor: 17.694

4.  Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.

Authors:  Sarah Livesley; Alistair J Sterling; Craig M Robertson; William R F Goundry; James A Morris; Fernanda Duarte; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-26       Impact factor: 16.823

5.  A droplet microfluidic platform for high-throughput photochemical reaction discovery.

Authors:  Alexandra C Sun; Daniel J Steyer; Anthony R Allen; Emory M Payne; Robert T Kennedy; Corey R J Stephenson
Journal:  Nat Commun       Date:  2020-12-03       Impact factor: 14.919

6.  Enantioselective Organophotocatalytic Telescoped Synthesis of a Chiral Privileged Active Pharmaceutical Ingredient.

Authors:  Fabian Herbrik; Miguel Sanz; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  Chemistry       Date:  2022-05-04       Impact factor: 5.020

7.  Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings.

Authors:  Daniel C Salgueiro; Benjamin K Chi; Ilia A Guzei; Pablo García-Reynaga; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-05       Impact factor: 16.823

8.  Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination.

Authors:  Yangzhong Qin; Qilei Zhu; Rui Sun; Jacob M Ganley; Robert R Knowles; Daniel G Nocera
Journal:  J Am Chem Soc       Date:  2021-06-30       Impact factor: 16.383

9.  Rapid Optimization of Photoredox Reactions for Continuous-Flow Systems Using Microscale Batch Technology.

Authors:  María González-Esguevillas; David F Fernández; Juan A Rincón; Mario Barberis; Oscar de Frutos; Carlos Mateos; Susana García-Cerrada; Javier Agejas; David W C MacMillan
Journal:  ACS Cent Sci       Date:  2021-06-08       Impact factor: 14.553

10.  Accelerated and Scalable C(sp3)-H Amination via Decatungstate Photocatalysis Using a Flow Photoreactor Equipped with High-Intensity LEDs.

Authors:  Ting Wan; Zhenghui Wen; Gabriele Laudadio; Luca Capaldo; Rob Lammers; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Rémy Broersma; Timothy Noël
Journal:  ACS Cent Sci       Date:  2021-12-16       Impact factor: 14.553

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.