A facile optimization of diazotization and phase transfer catalyzed azo-coupling reactions in microreactors

Faith M. Akwi; Coos Bosma; Paul Watts

doi:10.1556/1846.2016.00003

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Journal of Flow Chemistry

Volume/Issue:: Volume 6: Issue 2

A facile optimization of diazotization and phase transfer catalyzed azo-coupling reactions in microreactors

Authors:

Faith M. Akwi

Faith M. Akwi Nelson Mandela Metropolitan University, University Way, Port Elizabeth 6031, South Africa

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Coos Bosma

Coos Bosma Nelson Mandela Metropolitan University, University Way, Port Elizabeth 6031, South Africa

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Paul Watts

Paul Watts Nelson Mandela Metropolitan University, University Way, Port Elizabeth 6031, South Africa

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Paul.Watts@nmmu.ac.za

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Pages:: 73–79

Online Publication Date:: Jun 2016

Publication Date:: 01 Jun 2016

Article Category:: Rapid Communication

DOI:: https://doi.org/10.1556/1846.2016.00003

Keywords:: diazotization; azo-coupling; phase transfer catalysis; microreactors

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Herein, we illustrate how microreactor technology can be used as a tool for reaction screening and optimization, in addition to improving the reaction chemistry. We report the in-situ generation of azo compounds by reactive quenching of diazonium intermediates in microreactors. This involves an electrophilic aromatic substitution reaction, namely, an azo-coupling reaction performed in continuous-flow systems in the presence of a phase transfer catalyst with great emphasis on compounds that do not easily couple. Capitalizing on the benefits of a large surface area and the short molecular diffusion distances observed in microreactors, in-situ phase transfer catalyzed azo-coupling reaction of diphenylamine to p-nitroaniline was investigated. A rapid and easy optimization protocol was established which yielded a 99%, 22%, and 33% conversion of diphenylamine, carbazole, and triphenylamine, respectively, in approximately 2.4 min.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)