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

K. Sateesh Reddy; Bandi Siva; S. Divya Reddy; N. Reddy Naresh; T. V. Pratap; B. Venkateswara Rao; Yi-An Hong; B. Vijaya Kumar; A. Krishnam Raju; P. Muralidhar Reddy; Anren Hu

doi:10.3390/molecules25092199

Molecules (May 2020)

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

K. Sateesh Reddy,
Bandi Siva,
S. Divya Reddy,
N. Reddy Naresh,
T. V. Pratap,
B. Venkateswara Rao,
Yi-An Hong,
B. Vijaya Kumar,
A. Krishnam Raju,
P. Muralidhar Reddy,
Anren Hu

Affiliations

K. Sateesh Reddy: Technology Development Center, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Hyderabad 500049, India
Bandi Siva: Laboratory for Bioanalytical Chemistry, Institute of Chemistry, University of Neuchatel, Avenue de Bellevaux 51, CH-2000 Neuchatel, Switzerland
S. Divya Reddy: Department of Pharmacy, University College of Technology, Osmania University, Hyderabad-500007, TS, India
N. Reddy Naresh: Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, TS, India
T. V. Pratap: Technology Development Center, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Hyderabad 500049, India
B. Venkateswara Rao: AU College of Engineering (A), Andhra University, Visakhapatnam 530003, India
Yi-An Hong: Department of Laboratory Medicine and Biotechnology, College of Medicine, Tzu-Chi University, Hualien 97004, Taiwan
B. Vijaya Kumar: Department of Chemistry, Nizam College, Osmania University, Hyderabad 500001, TS, India
A. Krishnam Raju: Department of Chemistry, Nizam College, Osmania University, Hyderabad 500001, TS, India
P. Muralidhar Reddy: Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, TS, India
Anren Hu: Department of Laboratory Medicine and Biotechnology, College of Medicine, Tzu-Chi University, Hualien 97004, Taiwan

DOI: https://doi.org/10.3390/molecules25092199
Journal volume & issue: Vol. 25, no. 9
p. 2199

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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