Monofluoroalkenylation of dimethylamino compounds through radical-radical cross-coupling
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...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
28 June 2016
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| In: |
Angewandte Chemie. International edition
Year: 2016, Volume: 55, Issue: 32, Pages: 9416-9421 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201602347 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/anie.201602347 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/anie.201602347/abstract 
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| Author Notes: | Jin Xie, Jintao Yu, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
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| 520 | |a 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. | ||
| 650 | 4 | |a C−H activation | |
| 650 | 4 | |a late-stage functionalization | |
| 650 | 4 | |a monofluoroalkenylation | |
| 650 | 4 | |a photoredox catalysis | |
| 650 | 4 | |a radical coupling | |
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