Transition metal-free hydrodefluorination of acid fluorides and organofluorines by Ph 3 GeH promoted by catalytic [Ph 3 C][B(C 6 F 5 ) 4 ]

It has been shown that the germane Ph3GeH converts aryl and aliphatic acid fluorides directly to their corresponding aldehydes without over-reduction via the conversion of Ph3GeH to the germylium cation [Ph3Ge]+ by a catalytic amount of the tritylium salt [Ph3C][B(C6F5)4]. Here, no transition metal...

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Published in:Chemical communications (Cambridge, England) England), 2019-09, Vol.55 (73), p.10852-10855
Main Authors: 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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Language:English
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Summary:It has been shown that the germane Ph3GeH converts aryl and aliphatic acid fluorides directly to their corresponding aldehydes without over-reduction via the conversion of Ph3GeH to the germylium cation [Ph3Ge]+ by a catalytic amount of the tritylium salt [Ph3C][B(C6F5)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.
ISSN:1359-7345
1364-548X
DOI:10.1039/C9CC05075B