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  • Title: Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling.
    Author: Xie J, Yu J, Rudolph M, Rominger F, Hashmi AS.
    Journal: Angew Chem Int Ed Engl; 2016 Aug 01; 55(32):9416-21. PubMed ID: 27351709.
    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.
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