Metathesis Reactions between Heavy d-8 Fluorides and I(III)-Pyridine Complexes

Article abstract of DOI:10.1021/acs.inorgchem.9b03125

The reaction between trans-[AuF₂(pyridine)₂]⁺ and [PhI(pyridine)₂]²⁺ results in the formation of PhIF₂ and [Au(pyridine)₄]³⁺. Investigation of the reaction pathway using model Pd and Pt analogues of the gold complex indicate that the most likely mechanism is attack by the Au-F onto the I(III), rather than a redox process. This demonstrates that the Au(III)-F fragment can behave in a nucleophilic manner even in a relatively electron-poor cationic complex.

Full text of DOI:10.1021/acs.inorgchem.9b03125

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Article
Metathesis Reactions between Heavy d‑8 Fluorides and I(III)−
Pyridine Complexes
Mohammad Albayer, Lachlan Sharp-Bucknall, Nilan Withanage, Georgina Armendariz-Vidales,
Conor F. Hogan, and Jason L. Dutton*
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ABSTRACT: The reaction between trans-[AuF2(pyridine)2]+ and [PhI(pyridine)2]2+ results in the formation of PhIF2 and
[Au(pyridine)4]3+. Investigation of the reaction pathway using model Pd and Pt analogues of the gold complex indicate that the most
likely mechanism is attack by the Au−F onto the I(III), rather than a redox process. This demonstrates that the Au(III)−F fragment
can behave in a nucleophilic manner even in a relatively electron-poor cationic complex.
phase AuF3 also features slightly shorter bonds, measured at
1.88−1.89 Å.10 Previously reported coordination complexes
feature the shortest bond of 1.95 Å with a more typical range
of 2−2.2 Å.1−3,11
INTRODUCTION
■
The chemistry of organometallic/coordination complexes of
Au(III) fluorides is an underdeveloped area. It has only been
within the past decade that complexes of Au(III)−F
compounds have been reported, and the number of structurally
characterized examples remains around a dozen (e.g., 1−4).1−7
In recent work led by Toste and Nevado in organometallic
compounds such as 1−3, it has been shown that the Au(III)−
F bond may be displaced by boronic acids, leading to reductive
elimination and bond formation reactions which indicates
potential utility for the Au−F bond.1,2 In addition to the
structurally characterized examples, Riedel and co-workers
have studied the solution phase chemistry of pyridine−AuF3
mixtures.8 Our own entry into the area involved the synthesis
of pyridine ligated trans-bis-fluorides 7Au, from either Au(I) 5
or Au(III) 6Au_CN starting materials,9 which are the second
trans examples reported shortly after the work of Orduna and
co-workers on the synthesis of 4.4 Our work added the feature
that the complexes could be made from Au(III) and simple KF
rather than the XeF2 most often used in previous works. XeF2
can also be used to access the compounds from Au(I)
precursors in our system (Scheme 1). 7Au features the shortest
Au−F bonds in a coordination or organometallic complex
structurally characterized to date at 1.90 Å. The [AuF4]− anion
as tetra alkyl ammonium salts have been crystallographically
characterized to have Au−F bonds of 1.899−1.901 Å.8 Gas
Fluoride ligands are often utilized or required for the
stabilization of ultrahigh oxidation state metal centers. Given
the stability of our Au(III)−F system, we wondered if it was
possible to generate a Au(V) coordination complex from 7Au
using the pyridine ligated I(III) oxidant 8 (Weiss’ reagent,
[PhI(pyridine)2][OTf]2). Iodine(III) oxidant 8 is used to
generate Au(III) complexes 6Au, and our group has shown
that they can be used to generate d-8 Pt(IV) and (transiently)
Pd(IV) pyridine coordination complexes.12,13 Ritter and co-
workers were able to isolate Pd(IV) complexes using [PhI(4-
cyanopyridine)2][OTf]2 and a chelating pyrazine borate
ligand.14 In the attempt described here, we discovered a new
fluoride−pyridine metathesis reaction between Au(III) and
I(III), as well as for the d-8 Pd(II) and Pt(II) analogues.
Received: October 24, 2019
https://dx.doi.org/10.1021/acs.inorgchem.9b03125
© XXXX American Chemical Society
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Scheme 1. Synthesis of Au(III)−F Complex 7Au
Scheme 2. Reaction of 7Au with 8
Scheme 3. Potential Au(V) Intermediated Pathway for the Generation of 6Au and PhIF2
The results obtained from this reaction raise a question as to
whether the observed products were being mediated by
oxidation of Au(III) to a Au(V), as the chemistry of 8 with
RESULTS AND DISCUSSION
■
Treatment of 7Au with one equivalent of 8 in CD3CN resulted
in an instant color change from pale to deep yellow (Scheme
2). The 19F NMR signal arising from Au(III)−F in 7
disappeared, and a new signal appeared at −176 ppm. This
chemical shift is consistent with PhIF2.14,15 The solvent was
removed in vacuo followed by the addition of CDCl3, giving a
white solid which was filtered and redissolved in CD3CN. The
1H NMR spectrum of the solid redissolved in CD3CN
contained signals consistent with compound 6Au previously
transition metals is dominated by oxidative processes.18
A
possible mechanism based on the products is oxidation to a d-6
intermediate (9Au), followed by oxidative fluorination of PhI
generated in the oxidation to give the final products (Scheme
3). 8 is known to be able to oxidize d-8 Pd(II) or Pt(II)
compounds to give d-6, +4 oxidation state products or
intermediates.13,14
Given the extremely high reduction potential for Au(V), it
would be also possible for the pyridine ligands to become
oxidized.
reported by our lab,15 while the H and 19F NMR spectra of
1
the filtrate contained signals consistent with PhIF2.16,17
1
Analysis of the in situ H NMR spectrum of the reaction
mixture in CD3CN showed a 1:0.75 ratio of 6Au to PhIF2.
B
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To provide a further insight into the possible pathway of this
outcome, analogous Pd(II) and Pt(II) complexes were
examined (compounds 7Pd and 7Pt) as isoelectronic models
for Au(III) with accessible d-6 oxidation states to be reacted
with 8. Compound 7Pd was synthesized according to a
literature procedure,19 while 7Pt had not been previously
reported and was synthesized mimicking the synthetic protocol
used to access 7Pd. Isolation and X-ray characterization of 7Pt
revealed a cis-geometry for the respective pyridine and fluoride
ligands, as shown in Figure 1. Surprisingly, there is only one
structurally characterized Pt(II)−F complex with a similar
structural motif, with PPh3 ligands rather than pyridine.20
The reaction of Pt(II) compound 7Pt with 8 was attempted
in CDCl3 and led to a yellow solid (Scheme 5) which was
isolated and washed with CH2Cl2. The 19F NMR spectrum of
the isolated solid in CD3CN contained a singlet at −267 ppm
(JPt−F(satellite) = 1745 Hz for the 195Pt satellites) consistent with
the reported compound 9Pt,22 which was also confirmed by
proton NMR and mass spectrometry analysis. The 19F NMR
spectrum of the filtrate in CDCl3 contained a singlet at −178
ppm (consistent with PhIF2), and the proton NMR spectrum
of the filtrate contained signals consistent with 6Pt, PhIF2, and
PhI, which were confirmed by comparison with the reported
spectroscopic details of 6Pt22,23 or with genuine samples for
PhI and PhIF2. This result indicates that a d-6 compound
(9Pt) can be accessed from 7Pt and 8R and is therefore a
potential intermediate for the Pd and Au systems. The reaction
was rerun in CD3CN to ensure solubility of 9Pt to determine
in situ product ratios, which were found to be 1:0.75 for 6Pt/
9Pt based on integration of the 1H NMR spectrum. One other
species that could not be identified was apparent in the
aromatic region containing a phenyl group of the in situ
experiment.
As the critical control experiment, to investigate if these
outcomes are mediated via oxidative addition and then
oxidative fluorination of PhI or direct exchange, Pt(IV)
compound 9Pt was synthesized independently according to
literature procedures22 and was reacted with iodobenzene in
CH3CN, which resulted in no reaction. Reflux of the reaction
mixture for 3 h also resulted in no observable reaction based
on 19F NMR spectroscopy.
On this basis, we propose that the products observed in the
reaction of Au(III) and Pd(II) with I(III) reagents are
generated via a direct metathesis reaction, rather than via
reductive elimination from a d-6 intermediate. In the case of
Pt(II) reaction with I(III), the observed product distribution is
generated due to two competing reactions, i.e., the oxidation of
Pt(II) to Pt(IV) to give 9Pt which allowed for the greater
accessibility of Pt(IV) as compared to Pd(IV)/Au(V) and the
metathesis between Pt(II) and I(III) to give PhIF2 and 6Pt.
Results from electrochemistry experiments are in line with
the synthetic results. In DMSO solution, 7Pt undergoes an
irreversible oxidation at +0.85 V (vs Fc/Fc+). For the
corresponding Au compound no oxidation is seen to the
solvent limit. Upon repeating the experiment in MeCN for the
Au compound to use a wider potential window, no oxidation is
observed out to the solvent limit of +2.75 V (vs Fc/Fc+) .
Theoretical calculations at the MP2/LANL2DZ level of
theory using an CH3CN solvent force field show that the
observed reaction for Au has a ΔG of −57 kJ/mol. Oxidation
Figure 1. Solid-state structure of 7Pt. Thermal ellipsoids are depicted
at the 50% probability level. Selected bond distances (Å): Pt1−F1
1.986(4), Pt1−N1 1.996(7).
Pd(II) compound 7Pd was stirred with I(III) reagent 8 in
CDCl3 for 2 h. Proton and 19F NMR spectra of the reaction
mixture indicated the presence of PhIF2. Compound 6Pd was
1
also detected in H NMR and mass spectrometry ([m/z]+ =
211) results, which was confirmed by comparison with
reported spectroscopic details (Scheme 4).21 The ratio of
6Pd and PhIF2 in the reaction mixture was 1:1 as determined
1
by integration of the H NMR spectrum.
Scheme 4. Reaction of 7Pd with 8
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Scheme 5. Reaction of 7Pt with 8
to an Au(V) analogue of 9Pt is unfavorable by 90 kJ/mol. A
transition state to an Au(V) could not be found but must be
higher than the 90 kJ/mol increase in energy. The observed
rapid room temperature reaction rules out a barrier of this
magnitude on the way to such a potential intermediate. For Pt,
the ΔG to 9Pt is −292 kJ/mol, and conversion to 6Pt from the
starting material is less favorable at −164 kJ/mol. The
observed distribution of products thus suggests that the two
processes are kinetically similar. For Pd the oxidation is also
thermodynamically favorable at −171 kJ/mol, consistent with
the known ability of I(III) reagents to oxidize Pd(II)
complexes.24 The observed reaction leading to 6Pd is also
favorable, but less so at −102 kJ/mol, indicating that oxidation
for Pd is kinetically suppressed.
Ruling out an oxidation event at the Au atom, this leaves the
most likely mechanism for the reaction to be nucleophilic
attack on the I(III) center by the Au−F moiety. To investigate
whether 8 could potentially react with nucleophilic fluoride to
give PhIF2, reactions with KF were carried out.
To a solution of 8 in CH3CN was added 2 equiv of KF and 6
equiv of 18-crown-6. After 30 min, an aliquot was removed for
19F NMR spectroscopy which showed clean formation of
PhIF2 (Scheme 6). The solvent was removed in vacuo, and the
iodine atom in Weiss’ reagent that does not involve a redox
process. The only other example of a non-redox reaction at
iodine in this class of reagent is ligand exchange from one type
of pyridine to another reported by our group in 2012.27 The
iodine atom can also act as an electrophile in electrophilic
aromatic substitution reactions but becomes 2-coordinate.28,29
In the context of the group 10 chemistry described above,
the results of this reaction indicate that free fluoride
contaminant is an unlikely cause of the reaction, as exogenous
18-crown-6 must be added. Also, identical results are obtained
using 7Au synthesized from XeF2 rather than KF, making
contamination from excess fluoride unlikely, especially given
the quantitative nature of the transformation. Compound 7Au
has been shown not to react with free pyridine, making labile
pyridine from 8 in solution implausible as the agent to initiate
the transformation, as well as the I(III) center losing pyridine
in a non-reductive process being highly unfavorable. This
leaves nucleophilic attack by the Au−F on I(III) as the most
likely, albeit surprising, mechanism given the highly electro-
philic nature of cationic Au(III).
CONCLUSIONS
■
Here, we have demonstrated that even though it is bound to a
charged Au(III), the fluoride in 7Au is sufficiently nucleophilic
to replace pyridine on a coordinatively saturated I(III) and that
despite the apparent good stability of 7Au, it is reactive enough
to generate a relatively high energy compound in PhIF2. It is
also shown that this reactivity is common to the Pd(II) and
Pt(II) analogous M−F complexes, albeit with oxidation to
Pt(IV), a competing reaction for that metal. From the iodine
angle, this work is a rare example of non-redox chemistry
occurring at the iodine center in Weiss’ reagent.
Scheme 6. Direct Reaction of 8 with Fluoride
ASSOCIATED CONTENT
■
sı
* Supporting Information
residue was washed with Et2O to yield a white solid. A sample
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.inorgchem.9b03125.
1
of the solid redissolved in CD3CN gave resonances in the H
NMR and 19F NMR spectra consistent with PhIF2 which was
isolated in 67% yield.
Experimental procedures; NMR spectra of reaction
mixtures and isolated compounds; Cartersian coordi-
nates and electronic energies of calculated species; and
electrochemical experimental details (PDF)
This reaction is interesting from two perspectives, i.e., one as
a route to PhIF2 that does not involve HF or an exogenous
oxidant25,26 and second as a rare example of chemistry at the
D
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Accession Codes
CCDC 1956622 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
data_request@ccdc.cam.ac.uk, or by contacting The Cam-
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
Jason L. Dutton − Department of Chemistry and Physics, La
Trobe Institute for Molecular Science, La Trobe University,
Melbourne 3086, Victoria, Australia; orcid.org/0000-0002-
0361-4441; Email: j.dutton@latrobe.edu.au
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Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for
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Wilson, D. J. D.; Hulett, M. D.; Barnard, P. J.; Dutton, J. L. Access to
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Mohammad Albayer − Department of Chemistry and Physics,
La Trobe Institute for Molecular Science, La Trobe University,
Melbourne 3086, Victoria, Australia
Lachlan Sharp-Bucknall − Department of Chemistry and
Physics, La Trobe Institute for Molecular Science, La Trobe
University, Melbourne 3086, Victoria, Australia
Nilan Withanage − Department of Chemistry and Physics, La
Trobe Institute for Molecular Science, La Trobe University,
Melbourne 3086, Victoria, Australia
Georgina Armendariz-Vidales − Department of Chemistry and
Physics, La Trobe Institute for Molecular Science, La Trobe
University, Melbourne 3086, Victoria, Australia
Conor F. Hogan − Department of Chemistry and Physics, La
Trobe Institute for Molecular Science, La Trobe University,
Melbourne 3086, Victoria, Australia; orcid.org/0000-
0001-8250-3098
Complete contact information is available at:
https://pubs.acs.org/10.1021/acs.inorgchem.9b03125
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank La Trobe Institute for Molecular Science for their
generous funding of this project. This work is also supported
by an ARC Future Fellowship (J.L.D., FT16010007) and an
ARC Discovery Project (DP200100013).
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Chem. 2005, 44, 1547−1553.
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