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Issue 44, 2016
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Ligand-dependent formation of ion-pair CuI/CuIII trifluoromethyl complexes containing bisphosphines

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Abstract

We report novel ion-pair bisphosphine CuI/CuIII trifluoromethyl complexes [(P2)2CuI]+[CuIII(CF3)4] (P2 = DPPE, BINAP or Xantphos) featuring tetrahedral CuI and square planar CuIII units that are prepared via oxidative trifluoromethylation of CuI with CF3SiMe3 in the presence of AgF. The bisphosphine CuI/CuIII CF3 complexes are highly reactive for aerobic trifluoromethylation of arylboronic acids to produce trifluoromethylated arenes in good to quantitative yields, which is in sharp contrast to the CuI/CuIII complex with phen/PPh3 ligands (1′). These results not only provide strong evidence that both the neutral and ion-pair CuIII CF3 complexes are competent catalytic species for Cu-mediated oxidative trifluoromethylation reactions, but also have important mechanistic implications that the active catalyst and reaction mechanism should be distinct and ligand-dependent for trifluoromethylation reactions with different types of ancillary ligands.

Graphical abstract: Ligand-dependent formation of ion-pair CuI/CuIII trifluoromethyl complexes containing bisphosphines

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Publication details

The article was received on 29 Jul 2016, accepted on 26 Aug 2016 and first published on 26 Aug 2016


Article type: Communication
DOI: 10.1039/C6DT03016E
Citation: Dalton Trans., 2016,45, 17588-17592
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    Ligand-dependent formation of ion-pair CuI/CuIII trifluoromethyl complexes containing bisphosphines

    S. Zhang and W. Bie, Dalton Trans., 2016, 45, 17588
    DOI: 10.1039/C6DT03016E

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