Literature DB >> 28557142

Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis.

Zhenwei Wei1, Michael Wleklinski1, Christina Ferreira1, R Graham Cooks1.   

Abstract

Thin film formats are used to study the Claisen-Schmidt base-catalyzed condensation of 6-hydroxy-1-indanone with substituted benzaldehydes and to compare the reaction acceleration relative to the bulk. Relative acceleration factors initially exceeded 103 and were on the order of 102 at steady state, although the confined volume reaction was not electrostatically driven. Substituent effects were muted compared to those in the corresponding bulk and microdroplet reactions and it is concluded that the rate-limiting step at steady state is reagent transport to the interface. Conditions were found that allowed product deposition from the thin film to occur continuously as the reaction mixture was added and as the solvent evaporated. Yields of 74 % and production rates of 98 mg h-1 were reached in a very simple experimental system that could be multiplexed to greater scales.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  confined-volume reactions; mass spectrometry; reaction acceleration; spray-based ionization; thin films

Year:  2017        PMID: 28557142     DOI: 10.1002/anie.201704520

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


  10 in total

1.  Screening of the Suzuki Cross-Coupling Reaction Using Desorption Electrospray Ionization in High-Throughput and in Leidenfrost Droplet Experiments.

Authors:  Patrick W Fedick; Kiran Iyer; Zhenwei Wei; Larisa Avramova; Grace O Capek; R Graham Cooks
Journal:  J Am Soc Mass Spectrom       Date:  2019-08-08       Impact factor: 3.109

2.  Reaction Acceleration in Electrospray Droplets: Size, Distance, and Surfactant Effects.

Authors:  Brett M Marsh; Kiran Iyer; R Graham Cooks
Journal:  J Am Soc Mass Spectrom       Date:  2019-08-13       Impact factor: 3.109

3.  Microdroplets Accelerate Ring Opening of Epoxides.

Authors:  Yin-Hung Lai; Shyam Sathyamoorthi; Ryan M Bain; Richard N Zare
Journal:  J Am Soc Mass Spectrom       Date:  2018-03-22       Impact factor: 3.109

4.  Reaction of chloroauric acid with histidine in microdroplets yields a catalytic Au-(His)2 complex.

Authors:  Kai Luo; Jia Li; Yufei Cao; Chengyuan Liu; Jun Ge; Hao Chen; Richard N Zare
Journal:  Chem Sci       Date:  2020-01-31       Impact factor: 9.825

5.  High-yield gram-scale organic synthesis using accelerated microdroplet/thin film reactions with solvent recycling.

Authors:  Honggang Nie; Zhenwei Wei; Lingqi Qiu; Xingshuo Chen; Dylan T Holden; R Graham Cooks
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

6.  High yield accelerated reactions in nonvolatile microthin films: chemical derivatization for analysis of single-cell intracellular fluid.

Authors:  Zhenwei Wei; Xiaochao Zhang; Jinyu Wang; Sichun Zhang; Xinrong Zhang; R Graham Cooks
Journal:  Chem Sci       Date:  2018-08-21       Impact factor: 9.825

7.  Spontaneous Water Radical Cation Oxidation at Double Bonds in Microdroplets.

Authors:  Lingqi Qiu; Nicolás M Morato; Kai-Hung Huang; R Graham Cooks
Journal:  Front Chem       Date:  2022-04-26       Impact factor: 5.545

8.  Accelerated microdroplet synthesis of benzimidazoles by nucleophilic addition to protonated carboxylic acids.

Authors:  Pallab Basuri; L Edwin Gonzalez; Nicolás M Morato; Thalappil Pradeep; R Graham Cooks
Journal:  Chem Sci       Date:  2020-07-14       Impact factor: 9.825

9.  An integrated mass spectrometry platform enables picomole-scale real-time electrosynthetic reaction screening and discovery.

Authors:  Qiongqiong Wan; Suming Chen; Abraham K Badu-Tawiah
Journal:  Chem Sci       Date:  2018-05-30       Impact factor: 9.825

10.  N-Substituted Auxiliaries for Aerobic Dehydrogenation of Tetrahydro-isoquinoline: A Theory-Guided Photo-Catalytic Design.

Authors:  Savithra Jayaraj; Abraham K Badu-Tawiah
Journal:  Sci Rep       Date:  2019-08-02       Impact factor: 4.379

  10 in total

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