title: Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling.
abstract: An unprecedented and challenging radical-radical cross-coupling of α-aminoalkyl radicals with monofluoroalkenyl radicals derived from gem-difluoroalkenes was achieved. This first example of tandem C(sp(3) )-H and C(sp(2) )-F bond functionalization through visible-light photoredox catalysis offers a facile and flexible access to privileged tetrasubstituted monofluoroalkenes under very mild reaction conditions. The striking features of this redox-neutral method in terms of scope, functional-group tolerance, and regioselectivity are illustrated by the late-stage fluoroalkenylation of complex molecular architectures such as bioactive (+)-diltiazem, rosiglitazone, dihydroartemisinin, oleanic acid, and androsterone derivatives, which represent important new α-amino C-H monofluoroalkenylations.
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: Jintao
authors.initials: J
authors.lastname: Yu
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: 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. hashmi@hashmi.de.|Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), 21589, Jeddah, Saudi Arabia. hashmi@hashmi.de.
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
keywords: C−H activation; late-stage functionalization; monofluoroalkenylation; photoredox catalysis; radical coupling