Cu Photoredox Catalysts Supported by a 4,6-Disubstituted 2,2 '-Bipyridine Ligand: Application in Chlorotrifluoromethylation of Alkenes

Interest in base metal catalysis motivates the development of Cu-based photoredox catalysts for organic synthesis. However, only a few Cu catalysts have been applied in photoredox reactions, the majority of which contain one or two 1,10-phenanthroline ligands. Here we design a 4,6-disubstituted 2,2'-bipyridine ligand for Cu. Two heteroleptic [Cu(N<^>N)(P<^>P)][PF6] complexes, where N<^>N stands for the 2,2'-bipyridine ligand and P<^>P stands for a bisphosphine ligand, have been synthesized and characterized. They exhibit longer excited state lifetimes and higher Cu(I) / Cu(II) potentials compared to the most widely used Cu catalyst, [Cu-(dap)(2)]Cl. The complex with Xantphos as the P<^>P ligand is an efficient catalyst for chlorotrifluoromethylation of terminal alkenes, especially styrenes, which had been challenging substrates for previously reported photoredox reactions. This chlorotrifluoromethylation method enables the convenient introduction of a trifluoromethyl group into organic molecules under mild conditions, which is important for medicinal chemistry.


Published in:
Organometallics, 37, 21, 3928-3935
Year:
Nov 12 2018
ISSN:
0276-7333
1520-6041
Keywords:
Laboratories:


Note: The status of this file is: Anyone


 Record created 2018-12-13, last modified 2019-06-19

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