Flow Hydrodediazoniation of Aromatic Heterocycles

Röder, Liesa; Nicholls, Alexander J.; Baxendale, Ian R.

Abstract

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.

Citation

Röder, L., Nicholls, A. J., & Baxendale, I. R. (2019). Flow Hydrodediazoniation of Aromatic Heterocycles. Molecules, 24(10), Article 1996. https://doi.org/10.3390/molecules24101996

• Journal Article Type: Article
• Acceptance Date: May 22, 2019
• Online Publication Date: May 24, 2019
• Publication Date: May 31, 2019
• Deposit Date: May 24, 2019
• Publicly Available Date: May 28, 2019
• Journal: Molecules
• Electronic ISSN: 1420-3049
• Publisher: MDPI
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 10
• Article Number: 1996
• DOI: https://doi.org/10.3390/molecules24101996
• Public URL: https://durham-repository.worktribe.com/output/1300709