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Gold-catalyzed highly selective photoredox C(sp2)-H difluoroalkylation and perfluoroalkylation of hydrazones

The first gold-catalyzed photoredox C(sp2)-H difluoroalkylation and perfluoroalkylation of hydrazones with readily available RF-Br reagents is reported. The resulting gem-difluoromethylated and perfluoroalkylated hydrazones are highly functionalized, versatile molecules. A mild reduction of the coup...

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Bibliographic Details
Main Authors: Xie, Jin (Author) , Zhang, Tuo (Author) , Chen, Fei (Author) , Mehrkens, Nina (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 21 January 2016
In: Angewandte Chemie. International edition
Year: 2016, Volume: 55, Issue: 8, Pages: 2934-2938
ISSN:1521-3773
DOI:10.1002/anie.201508622
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201508622
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/anie.201508622/abstract
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Author Notes:Jin Xie, Tuo Zhang, Fei Chen, Nina Mehrkens, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi
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Summary:The first gold-catalyzed photoredox C(sp2)-H difluoroalkylation and perfluoroalkylation of hydrazones with readily available RF-Br reagents is reported. The resulting gem-difluoromethylated and perfluoroalkylated hydrazones are highly functionalized, versatile molecules. A mild reduction of the coupling products can efficiently produce gem-difluoromethylated β-amino phosphonic acids and β-amino acid derivatives. In mechanistic studies, a difluoroalkyl radical intermediate was detected by an EPR spin-trapping experiment, indicating that a gold-catalyzed radical pathway is operating.
Item Description:Gesehen am 29.09.2017
Im Titel ist "2" hochgestellt
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201508622

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