Issue 98, 2022
From the journal:

Chemical Communications

Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles†‡

Nathan T. Coles, ORCID logo *ab   Lucie J. Groth,a   Lea Dettling, ORCID logo a   Daniel S. Frost, ORCID logo a   Massimo Rigo,a   Samuel E. Neale ORCID logo *c  and  Christian Müller ORCID logo *a  

* Corresponding authors

a Institute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstr. 34/36, 14195 Berlin, Germany
E-mail: c.mueller@fu-berlin.de

b School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
E-mail: Nathan.Coles@nottingham.ac.uk

c Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
E-mail: sen36@bath.ac.uk

Abstract

An unexpected route to hitherto unknown amidine-functionalized phosphinines has been developed that is rapid and simple. Starting from primary amines and CF3-substituted λ3,σ2-phosphinines, a cascade of dehydrofluorination reactions leads selectively to ortho-amidinephosphinines. DFT calculations reveal that this unusual transformation can take place via a series of nucleophilic attacks at the electrophilic, low-coordinate phosphorus atom.

Graphical abstract: Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles

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Article information

DOI
https://doi.org/10.1039/D2CC05178H
Article type
Communication
Submitted
20 Sep 2022
Accepted
03 Nov 2022
First published
03 Nov 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 13580-13583

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Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles

N. T. Coles, L. J. Groth, L. Dettling, D. S. Frost, M. Rigo, S. E. Neale and C. Müller, Chem. Commun., 2022, 58, 13580 DOI: 10.1039/D2CC05178H

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