Gold Catalysts with Polyaromatic-NHC ligands. Enhancement of Activity by Addition of Pyrene
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http://dx.doi.org/10.1021/acs.organomet.7b00172 |
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Title
Gold Catalysts with Polyaromatic-NHC ligands. Enhancement of Activity by Addition of PyreneDate
2017Publisher
American Chemical SocietyISSN
0276-7333; 1520-6041Bibliographic citation
Gold Catalysts with Polyaromatic-NHC ligands. Enhancement of Activity by Addition of Pyrene Susana Ibáñez, Macarena Poyatos, and Eduardo Peris Organometallics 2017 36 (7), 1447-1451 DOI: 10.1021/acs.organomet.7b00172Type
info:eu-repo/semantics/articlePublisher version
http://pubs.acs.org/doi/abs/10.1021/acs.organomet.7b00172Abstract
Three Au(I) complexes with N-heterocyclic carbene ligands
fused to polycyclic aromatic hydrocarbons (pyrene and phenanthrophenazine)
have been obtained and fully characterized. The complexes were tested
as catalysts ... [+]
Three Au(I) complexes with N-heterocyclic carbene ligands
fused to polycyclic aromatic hydrocarbons (pyrene and phenanthrophenazine)
have been obtained and fully characterized. The complexes were tested
as catalysts in the hydroamination of terminal alkynes, where they showed
moderate to good activity. The addition of a catalytic amount of pyrene to the
reaction mixtures produced an improvement in the performance of the
catalysts. The study of the reaction order of the catalyst in this reaction
indicated that the order is 0.5, indicating that an off-cycle inactive catalyst
dimer is formed, as consequence of the self-association of the complex by π−π
stacking interactions. The reaction order in catalyst when pyrene is added to
the reaction mixture is 1 > n > 0.5, therefore being higher than that in the
absence of pyrene. Studies made by 1
H NMR spectroscopy demonstrate that
an important self-association of the catalyst occurs at the concentrations used
in the catalytic reactions. The association of pyrene with the catalyst was also
observed and quantified by 1
H NMR titrations. The studies allowed us to conclude that pyrene influences the activity of the
Au(I) catalysts due to reasons related to the modification of the reaction order in the catalyst rather than to allosteric issues. [-]
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Organometallics 2017, 36, 1447−1451Rights
© 2017 American Chemical Society
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