Premium
Gold‐Catalyzed Highly Selective Photoredox C(sp 2 )−H Difluoroalkylation and Perfluoroalkylation of Hydrazones
Author(s) -
Xie Jin,
Zhang Tuo,
Chen Fei,
Mehrkens Nina,
Rominger Frank,
Rudolph Matthias,
Hashmi A. Stephen K.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508622
Subject(s) - reagent , chemistry , photoredox catalysis , catalysis , combinatorial chemistry , electron paramagnetic resonance , medicinal chemistry , organic chemistry , photochemistry , photocatalysis , physics , nuclear magnetic resonance
The first gold‐catalyzed photoredox C(sp 2 )−H difluoroalkylation and perfluoroalkylation of hydrazones with readily available R F −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.