Flow Hydrodediazoniation of Aromatic Heterocycles
1
Department of Biology, Chemistry, and Pharmacy, Freie Universität Berlin, 14195 Berlin, Germany
2
Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Maurizio Benaglia
Molecules 2019, 24(10), 1996; https://doi.org/10.3390/molecules24101996
Received: 29 April 2019 / Revised: 20 May 2019 / Accepted: 22 May 2019 / Published: 24 May 2019
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system.
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Keywords:
flow chemistry; continuous processing; deamination; hydrodediazoniation; heterocylic; isopentyl nitrite
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MDPI and ACS Style
Röder, L.; Nicholls, A.J.; Baxendale, I.R. Flow Hydrodediazoniation of Aromatic Heterocycles. Molecules 2019, 24, 1996.
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