An unexpected route to hitherto unknown amidine-functionalized phosphinines has been developed that is rapid and simple. Starting from primary amines and CF-substituted λ,σ-phosphinines, a cascade of dehydrofluorination reactions leads selectively to -amidinephosphinines. DFT calculations reveal that this unusual transformation can take place a series of nucleophilic attacks at the electrophilic, low-coordinate phosphorus atom.
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Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles.
Chem Commun (Camb)
December 2022
Institute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstr. 34/36, 14195 Berlin, Germany.
An unexpected route to hitherto unknown amidine-functionalized phosphinines has been developed that is rapid and simple. Starting from primary amines and CF-substituted λ,σ-phosphinines, a cascade of dehydrofluorination reactions leads selectively to -amidinephosphinines. DFT calculations reveal that this unusual transformation can take place a series of nucleophilic attacks at the electrophilic, low-coordinate phosphorus atom.
View Article and Find Full Text PDFThe hydrofluoroolefin -1,3,3,3-tetrafluoropropene has been activated an initial C-F bond activation and subsequent C-H bond activation using [Rh(H)(PEt)] (1) or C-H bond activation at [Rh(CH)(PEt)] (8). In both cases the formation of [Rh{()-CF[double bond, length as m-dash]CHCF}(PEt)] (3) was observed. Importantly, the C-F activation product [Rh{()-CH[double bond, length as m-dash]CHCF}(PEt)] (2) reacts in the presence of -1,3,3,3-tetrafluoropropene into 3.
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