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Monofluoroalkenylation of Dimethylamino Compounds through Radical–Radical Cross‐Coupling
Author(s) -
Xie Jin,
Yu Jintao,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602347
Subject(s) - radical , chemistry , regioselectivity , combinatorial chemistry , photoredox catalysis , functional group , coupling reaction , photochemistry , radical ion , catalysis , organic chemistry , photocatalysis , ion , polymer
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.