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Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy

Aims and Objectives The establishment of a green and sustainable Knoevenagel condensation reaction in organic chemistry is still crucial. This work aimed to provide a newly developed metal-free and halogen-free catalytic methodology for the synthesis of CS and (hetero-)arylidene malononitriles in th...

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Main Authors: Johari, Suzaimi, Johan, Mohd Rafie, Khaligh, Nader Ghaffari
Format: Article
Published: Bentham Science Publishers 2024
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/45866/
https://doi.org/10.2174/0115701794268766231108110816
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spelling my.um.eprints.458662024-11-13T04:26:32Z http://eprints.um.edu.my/45866/ Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy Johari, Suzaimi Johan, Mohd Rafie Khaligh, Nader Ghaffari QD Chemistry Aims and Objectives The establishment of a green and sustainable Knoevenagel condensation reaction in organic chemistry is still crucial. This work aimed to provide a newly developed metal-free and halogen-free catalytic methodology for the synthesis of CS and (hetero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensation reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts.Materials and Methods A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach.Results The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the residue solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crystalline products with 95 +/- 2% yield in five consecutive runs.Conclusion Energy efficiency, cost saving, greener conditions, using only 5 mol% of organocatalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system. Bentham Science Publishers 2024 Article PeerReviewed Johari, Suzaimi and Johan, Mohd Rafie and Khaligh, Nader Ghaffari (2024) Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy. Current Organic Synthesis, 21 (5). pp. 704-716. ISSN 1570-1794, DOI https://doi.org/10.2174/0115701794268766231108110816 <https://doi.org/10.2174/0115701794268766231108110816>. https://doi.org/10.2174/0115701794268766231108110816 10.2174/0115701794268766231108110816
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Johari, Suzaimi
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
description Aims and Objectives The establishment of a green and sustainable Knoevenagel condensation reaction in organic chemistry is still crucial. This work aimed to provide a newly developed metal-free and halogen-free catalytic methodology for the synthesis of CS and (hetero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensation reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts.Materials and Methods A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach.Results The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the residue solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crystalline products with 95 +/- 2% yield in five consecutive runs.Conclusion Energy efficiency, cost saving, greener conditions, using only 5 mol% of organocatalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system.
format Article
author Johari, Suzaimi
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_facet Johari, Suzaimi
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_sort Johari, Suzaimi
title Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
title_short Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
title_full Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
title_fullStr Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
title_full_unstemmed Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy
title_sort organocatalytic synthesis of (hetero)arylidene malononitriles using a more sustainable, greener, and scalable strategy
publisher Bentham Science Publishers
publishDate 2024
url http://eprints.um.edu.my/45866/
https://doi.org/10.2174/0115701794268766231108110816
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score 13.223943

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