Monofluoroalkenylation of Dimethylamino Compounds through Radical–Radical Cross‐Coupling |
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| Authors: | Dr Jin Xie Dr Jintao Yu Dr Matthias Rudolph Dr Frank Rominger Prof Dr A Stephen K Hashmi |
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| Affiliation: | 1. http://www.hashmi.de;2. Organisch-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: | 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(sp3)?H and C(sp2)?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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| Keywords: | late-stage functionalization monofluoroalkenylation photoredox catalysis radical coupling C− H activation |
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