title: Gold-Catalyzed Highly Selective Photoredox C(sp(2) )-H Difluoroalkylation and Perfluoroalkylation of Hydrazones.
abstract: The first gold-catalyzed photoredox C(sp(2) )-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.
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Jin
authors.initials: J
authors.lastname: Xie
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Tuo
authors.initials: T
authors.lastname: Zhang
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Fei
authors.initials: F
authors.lastname: Chen
authors.affiliation: Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Nina
authors.initials: N
authors.lastname: Mehrkens
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Rudolph
authors.affiliation: Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, 21589, Saudi Arabia. hashmi@hashmi.de.
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
keywords: C−H functionalization; fluorine; gold catalysis; photocatalysis