Transition metal-free hydrodefluorination of acid fluorides and organofluorines by PhGeH promoted by catalytic [PhC][B(CF)]

It has been shown that the germane Ph 3 GeH converts aryl and aliphatic acid fluorides directly to their corresponding aldehydes without over-reduction via the conversion of Ph 3 GeH to the germylium cation [Ph 3 Ge] + by a catalytic amount of the tritylium salt [Ph 3 C][B(C 6 F 5 ) 4 ]. Here, no tr...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-09, Vol.55 (73), p.1852-1855
Hauptverfasser: Hayatifar, Ardalan, Borrego, Alejandro, Bosek, David, Czarnecki, Matthew, Derocher, Gabriel, Kuplicki, Adam, Lytle, Erik, Padilla, Jonas, Paroly, Charles, Tubay, Gillian, Vyletel, Jackson, Weinert, Charles S
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Sprache:eng
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Zusammenfassung:It has been shown that the germane Ph 3 GeH converts aryl and aliphatic acid fluorides directly to their corresponding aldehydes without over-reduction via the conversion of Ph 3 GeH to the germylium cation [Ph 3 Ge] + by a catalytic amount of the tritylium salt [Ph 3 C][B(C 6 F 5 ) 4 ]. Here, no transition metal catalyst is required and there is no decarbonylation of the acid fluoride, which are advantages over existing methods. The fluorine atoms can also be abstracted from organofluorine compounds using this method. The germylium cation [Ph 3 Ge] + converts aryl and aliphatic acid fluorides directly to their corresponding aldehydes. Hydrodefluorination of organofluorine compounds by [Ph 3 Ge] + was also observed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc05075b