In Situ FTIR Spectroscopic Monitoring of the Formation of the Arene Diazonium Salts and its Applications to the Heck-Matsuda Reaction

This study depicts the use of a fiber-optic coupled Fourier transform infrared spectroscopy-attenuated total reflection (FTIR-ATR) probe for the in-depth study of arene diazonium salt formation and their utilization in the Heck-Matsuda reaction. The combination of these chemical reactions and in sit...

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Published inMolecules (Basel, Switzerland) Vol. 25; no. 9; p. 2199
Main Authors Reddy, K Sateesh, Siva, Bandi, Reddy, S Divya, Naresh, N Reddy, Pratap, T V, Rao, B Venkateswara, Hong, Yi-An, Kumar, B Vijaya, Raju, A Krishnam, Reddy, P Muralidhar, Hu, Anren
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 08.05.2020
MDPI
Subjects
Alcohols
arene diazonium salt
Automation
Chemical reactions
Data processing
Diazonium Compounds - chemical synthesis
Diazonium Compounds - chemistry
Fourier analysis
Fourier transforms
Heck–Matsuda reaction
High-performance liquid chromatography
in situ FTIR-ATR
Infrared reflection
Infrared spectroscopy
Intermediates
Liquid chromatography
Optical fibers
Organic chemicals
Process controls
Salt
Salts
Software
Spectroscopy, Fourier Transform Infrared
Spectrum analysis
Trends
Heck–Matsuda reaction
arene diazonium salt
In situ FTIR-ATR
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Summary:This study depicts the use of a fiber-optic coupled Fourier transform infrared spectroscopy-attenuated total reflection (FTIR-ATR) probe for the in-depth study of arene diazonium salt formation and their utilization in the Heck-Matsuda reaction. The combination of these chemical reactions and in situ IR spectroscopy enabled us to recognize the optimum parameters for arene diazonium salt formation and to track the concentrations of reactants, products and intermediates under actual reaction conditions without time consuming HPLC analysis and the necessity of collecting the sample amid the reaction. Overall advantages of the proposed methodology include precise reaction times as well as identification of keto enol tautomerization in allylic alcohols supporting the 'path a' elimination mechanism in the Heck-Matsuda reaction.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25092199