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

Nathan T. Coles; Lucie J. Groth; Lea Dettling; Daniel S. Frost; Massimo Rigo; Samuel E. Neale; Christian Müller

doi:10.1039/d2cc05178h

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

Nathan T. Coles, Lucie J. Groth, Lea Dettling, Daniel S. Frost, Massimo Rigo, Samuel E. Neale, Christian Müller

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (SciVal)

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.

Original language	English
Pages (from-to)	13580-13583
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	98
Early online date	3 Nov 2022
DOIs	https://doi.org/10.1039/d2cc05178h
Publication status	Published - 21 Dec 2022

Bibliographical note

No funders listed.

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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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.",

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T1 - Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles

AU - Coles, Nathan T.

AU - Groth, Lucie J.

AU - Dettling, Lea

AU - Frost, Daniel S.

AU - Rigo, Massimo

AU - Neale, Samuel E.

AU - Müller, Christian

N1 - No funders listed.

PY - 2022/12/21

Y1 - 2022/12/21

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85142441589

U2 - 10.1039/d2cc05178h

DO - 10.1039/d2cc05178h

M3 - Article

C2 - 36354311

AN - SCOPUS:85142441589

SN - 1359-7345

VL - 58

SP - 13580

EP - 13583

JO - Chemical Communications

JF - Chemical Communications

IS - 98

ER -

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

Abstract

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