Gold‐Catalyzed Highly Selective Photoredox C(sp2)−H Difluoroalkylation and Perfluoroalkylation of Hydrazones |
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| Authors: | Dr Jin Xie M?Sc Tuo Zhang M?Sc Fei Chen M?Sc Nina Mehrkens Dr Frank Rominger Dr Matthias Rudolph Prof?Dr A Stephen K Hashmi |
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| Institution: | 1. Organisch-Chemisches Institut, Universit?t Heidelberg, Heidelberg, Germany;2. Anorganisch-Chemisches Institut, Universit?t Heidelberg, Heidelberg, Germany;3. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, Saudi Arabia |
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| Abstract: | 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. |
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| Keywords: | C− H functionalization fluorine gold catalysis photocatalysis |
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