Pt-Me bond cleavage in the reactions of dimethylplatinum(II) complexes containing chelating phosphine ligands with organotin(IV) chlorides

Article abstract of DOI:10.1139/cjc-2013-0338

Selective Pt-Me bond activation of dimethylplatinum(II) complexes [PtMe₂(PP)] (PP = dppm (bis(diphenylphosphino)methane), dppe (1,2-bis(diphenylphosphino)ethane), dppp (1,3-bis(diphenylphosphino)propane)) was achieved by SnMe₂Cl₂ to yield the corresponding platinum(II) complexes [PtMeCl(PP)] (PP = dppm, dppe, dppp) and cis-[PtCl ₂(PP)] (PP = dppm, dppp). On the other hand, the reactions of complexes [PtMe₂(PP)] (PP = dppm, dppe, dppp) with SnPh₃Cl resulted in the selective cleavage of the Pt-Me bond to afford the methylplatinum(II) complexes [PtMeCl(PP)]. Notably, the reaction of [PtMe ₂(dppm)] with SnMe₂Cl₂ and SnPh₃Cl also gave the ionic A-frame complex [Pt₂Me₂(μ-Cl)(μ- dppm)₂]Cl. The variable-temperature ¹H and ³¹P NMR spectroscopy shows that the cleavage of the Pt-Me bond occurs very rapidly and the short-lived platinum(IV) intermediate is difficult to detect during the reaction. An explanation is presented on the basis of the nature of the strong π-acceptance of the phosphine ligand, which resulted in the formation of a very unstable platinum(IV) intermediate.

Full text of DOI:10.1139/cjc-2013-0338

1288
ARTICLE
Pt−Me bond cleavage in the reactions of dimethylplatinum(II)
complexes containing chelating phosphine ligands with
organotin(IV) chlorides
Badri Z. Momeni and Sedigheh Eatezadi
Abstract: Selective Pt−Me bond activation of dimethylplatinum(II) complexes [PtMe2(PP)] (PP = dppm (bis(diphenylphosphino)
methane), dppe (1,2-bis(diphenylphosphino)ethane), dppp (1,3-bis(diphenylphosphino)propane)) was achieved by SnMe2Cl2 to
yield the corresponding platinum(II) complexes [PtMeCl(PP)] (PP = dppm, dppe, dppp) and cis-[PtCl2(PP)] (PP = dppm, dppp). On the
other hand, the reactions of complexes [PtMe2(PP)] (PP = dppm, dppe, dppp) with SnPh3Cl resulted in the selective cleavage of the
Pt−Me bond to afford the methylplatinum(II) complexes [PtMeCl(PP)]. Notably, the reaction of [PtMe2(dppm)] with SnMe2Cl2 and
SnPh3Cl also gave the ionic A-frame complex [Pt2Me2(␮-Cl)(␮-dppm)2]Cl. The variable-temperature 1H and 31P NMR spectroscopy
shows that the cleavage of the Pt−Me bond occurs very rapidly and the short-lived platinum(IV) intermediate is difficult to detect
during the reaction. An explanation is presented on the basis of the nature of the strong ␲-acceptance of the phosphine ligand,
which resulted in the formation of a very unstable platinum(IV) intermediate.
Key words: platinum, tin, phosphine, mechanism, NMR.
Résumé : L’activation sélective de la liaison Pt−Me de complexes de diméthylplatine(II) [PtMe2(PP)] (PP = dppm (bis(diphénylphosphino)
méthane), dppe (1,2-bis(diphénylphosphino) éthane), dppp (1,3-bis(diphénylphosphino)propane)) par le SnMe2Cl2 conduit a` la forma-
tion des complexes de platine(II) correspondants [PtMeCl(PP)] (PP = dppm, dppe, dppp) et cis-[PtCl2(PP)] (PP = dppm, dppp). Par ailleurs,
les réactions des complexes [PtMe2(PP)] (PP = dppm, dppe, dppp) avec le SnPh3Cl aboutissent au clivage de la liaison Pt−Me pour donner
les complexes de méthylplatine(II) [PtMeCl(PP)]. En particulier, la réaction de [PtMe2(dppm)] avec le SnMe2Cl2 et le SnPh3Cl fournit
aussi le complexe ionique a` structure en A [Pt2Me2(␮-Cl)(␮-dppm)2]Cl. La spectroscopie NMR du 1H et du 31P a` température variable
montre que le clivage de la liaison Pt−Me est très rapide et qu’il est difficile de détecter l’éphémère complexe intermédiaire de
platine(IV) durant la réaction. On présente une explication fondée sur le caractère fortement ␲-accepteur du ligand phosphine, qui
conduit a` la formation d’un complexe intermédiaire de platine(IV) très instable. [Traduit par la Rédaction]
Mots-clés : platine, étain, phosphine, mécanisme, NMR.
a variety of examples in literature that the Pt−Me bond cleavage
Introduction
occurs from the six-coordinated platinum(IV) complexes resulting
The mechanism of electrophilic cleavage of the metal−carbon
from the oxidative addition reactions.18 The most definitive evi-
bond plays an important role in organometallic chemistry, mak-
dence for an oxidative addition/reductive elimination mechanism
ing it the subject of many studies over the last few decades.1–3 For
is the detection of a platinum(IV) intermediate.15 For example, the
example, the Stille reaction is a palladium(0)-catalyzed coupling
intermediacy of platinum(IV) hydride in the protonolysis of al-
of organostannanes with organic electrophiles of R−X that is suc-
kylplatinum(II) bonds is consistent with an oxidative addition/
reduction elimination mechanism.15
cessfully used in organic synthesis.4 The majority of the Pt−C bond
cleavage has been focused on the reactions of alkylplatinum com-
plexes containing phosphine ligands.5–8 For example, the reaction of
[PtMe2(phosphine)2] with iodine, magnesium iodide, or hydrogen
chloride is a facile synthetic route to the monomethylplatinum(II)
derivatives.9 However, less is known about the mechanism of the
carbon−heteroatom coupling reaction catalyzed by transition
metals.10–12 Notable catalytic C (sp3)−O reductive coupling of the
platinum(IV) center involved in the Shilov reaction affords the
alcohol or alkyl chloride from the low-cost alkanes.13
Two mechanisms have been proposed for the cleavage of the
Pt−Me bond by the electrophilic reagents. The first is the attack of
an electrophile at the metal center, giving an oxidative addition/
reductive elimination sequence (SE(ox) mechanism), while the sec-
ond is the direct attack at the Pt–C bond (SE2 mechanism).14–16
Despite the large amount of research conducted, it still remains
difficult to predict the selectivity of the site of attack.17 There are
There are a number of Sn(IV) halides that oxidatively add to
electron-rich platinum(II) complexes containing diimine ligands.18–21
Kuyper reported the first six-coordinated stannylplatinum(IV) com-
plexes from the reaction of the electron-rich dimethylplatinum(II)
complex [PtMe2(NN)] (NN = 2,2=-bipyridine, 1,10-phenanthroline,
2,9–dimethyl-4,7-diphenyl-1,10-phenenthroline) with SnRnCl4−n
(n = 0–3, R = Me, Ph).22 In some cases, there is an equilibrium that
is shifted towards platinum(II) complexes at room temperature.19
Interestingly, the halide ion in halostannylplatinum(IV) complexes
can act as a donor to the organotin(IV) halide because tin(IV) centers
can easily adopt trigonal bipyramidal or octahedral geometries.23
Similarly, the stannylplatinum(IV) complex containing the tridentate
nitrogen ligand of [Pt(SnMe2Cl)Me2{(pz)3BH-N,N=,N== }] ((pz)3BH−
=
tris(pyrazoyl-1-yl)borate) was prepared from the reaction of
platinum(II) complex K[PtMe2{(pz)3BH-N,N=}] with SnMe2Cl2.24 It
Received 30 July 2013. Accepted 16 September 2013.
B.Z. Momeni and S. Eatezadi. Department of Chemistry, K.N. Toosi University of Technology, P.O. Box 16315-1618, Tehran 15418, Iran.
Corresponding author: Badri Z. Momeni (e-mail: momeni@kntu.ac.ir).
Can. J. Chem. 91: 1288–1291 (2013) dx.doi.org/10.1139/cjc-2013-0338
Published at www.nrcresearchpress.com/cjc on 23 September 2013.

Momeni and Eatezadi
1289
Scheme 1.
has been reported that the organotin(IV) chlorides oxidatively
add to platinum(0) complexes containing phosphine ligands to
produce stannylplatinum(II) complexes.25 In this context, we un-
dertook a study of the reaction of a related series of dimeth-
ylplatinum(II) complexes containing chelating phosphine ligands
with organotin(IV) chlorides of SnMe2Cl2 and SnPh3Cl.
Experimental
Materials and instrumentation
All procedures were performed under an atmosphere of argon.
Dichloromethane was distilled from P2O5 and diethyl ether was
distilled from sodium/benzophenone ketyl. Acetone and the other
reagents were used without further purification. NMR data were
1
recorded using a Bruker Avance DRX 500 MHz spectrometer. H
and 31P NMR chemical shifts are reported relative to residual sol-
vent signal and 85% H3PO4, respectively. All of the chemical shifts
and coupling constants are reported in ppm and Hz, respectively.
The complexes [PtMe2(PP)] (PP = dppm, dppe, dppp) were prepared
according to the literature.26,27 The complexes [PtCl2(dppm)],28
[PtMeCl(PP)] (PP = dppm, dppe, dppp)16, and [Pt2Me2(␮-Cl)(␮-dppm)2]Cl26
were characterized according to the literature.
Reaction of [PtMe2(dppm)] with SnMe2Cl2
precooled probe of the NMR spectrometer at −84 °C and the 1H and
31P NMR spectra were obtained at 2–3 °C intervals from −84 to
+25 °C.
To a solution of [PtMe2(dppm)] (100 mg, 0.16 mmol) in acetone
(20 mL) was added SnMe2Cl2 (72 mg, 0.33 mmol). The solution
color changed to yellow and the solution was then stirred for
2 days. The solvent was removed and the resulting residue was
crystallized from CH2Cl2 − diethyl ether to form a pale yellow
solid, identified as a mixture of 2a (major product), 4a (minor
product), and 3a (minor product). Yield: 78%.
Results and discussion
The reaction of dimethylplatinum(II) complex [PtMe2(dppm)]
(1a) with SnMe2Cl2 in a Pt:Sn 1:2 molar ratio at room temperature
resulted in the formation of [PtMeCl(dppm)] (2a), [PtCl2(dppm)]
(3a), and [Pt2Me2(␮-Cl)(␮-dppm)2]Cl (4a) (Scheme 1). The products
were characterized based on the 1H and 31P NMR spectra.16,26,28
One would expect the platinum(IV) products resulting from an
oxidative addition reaction of the platinum(II) complex. Initial
attempts to detect the in situ platinum(IV) product resulting
from an oxidative addition reaction of [PtMe2(dppm)] (1a) with
SnMe2Cl2 at room temperature, which would give the character-
istic 2J(PtIVH) coupling constant, showed that no platinum(IV)
product formed during the reaction. The 1H and 31P NMR spectra
showed that a mixture of platinum(II) complexes 2a–4a persist in
solution that were essentially the same as the solid-state products
Reaction of [PtMe2(dppe)] with SnMe2Cl2
A mixture of [PtMe2(dppe)] (80 mg, 0.13 mmol) and SnMe2Cl2
(56 mg, 0.26 mmol) in acetone (20 mL) was stirred for 2 days. The
product was filtered off and washed with diethyl ether to give a
white solid, identified as 2b. Yield: 65%.
Reaction of [PtMe2(dppp)] with SnMe2Cl2
A mixture of of [PtMe2(dppp)] (90 mg, 0.14 mmol) and SnMe2Cl2
(62 mg, 0.28 mmol) in acetone (20 mL) was stirred for 2 days. The
product was filtered off and washed with diethyl ether to give a
white solid, identified as 2c (major product) and 3c (minor product).
Yield: 54%.
1
(Scheme 1). Therefore, the variable-temperature H and 31P NMR
spectra were obtained for the reaction of [PtMe2(dppm)] (1a) with
SnMe2Cl2 in acetone-d6 with an interval of 2–3 °C to detect if any
platinum(IV) intermediate forms during the reaction. Due to mon-
itoring the reaction with an interval of 2–3 °C, there were several
1H NMR spectra. Therefore, a set of selected variable 1H NMR spec-
tra for the reaction of 1a with SnMe2Cl2 in a 1:2 Pt:Sn molar ratio
is shown in Fig. 1. At −82.8 °C, the 1H NMR spectrum displayed two
distinct signals at ␦ = 0.82 and 1.11 ppm. The signal at ␦ = 0.82 ppm
appeared as a singlet with broad platinum satellites. This signal is
assigned to the presence of the [PtMe2(dppm)] in solution. The
Reaction of [PtMe2(dppm)] with SnPh3Cl
Following the same procedure as for the reaction of [PtMe2(dppm)]
with SnMe2Cl2, a mixture of [PtMe2(dppm)] (100 mg, 0.16 mmol) with
SnPh3Cl (126 mg, 0.33 mmol) was stirred for 3 days to give a pale
yellow solid, identified as 2a (major product) and 4a (minor prod-
uct). Yield: 68%.
Reaction of [PtMe2(dppe)] with SnPh3Cl
A mixture of [PtMe2(dppe)] (80 mg, 0.13 mmol) and SnPh3Cl
(99 mg, 0.26 mmol) in acetone (25 mL) was stirred for 3 days. The
solvent was removed and the resulting residue was crystallized
from CH2Cl2 − diethyl ether to form pale yellow crystals, identi-
fied as 2b. Yield: 76%.
2
signal at ␦ = 1.11 was flanked by tin satellites with J(119/117SnH) =
91 Hz due to the starting SnMe2Cl2. The magnitude of 2J(119/117SnH) =
91 Hz is considerably larger than that reported for a solution of
SnMe2Cl2 in CDCl3 (2J(119SnH) = 68.6 Hz, 2J(117SnH) = 65.7),29 typical
for the five-coordinated tin(IV) compounds.19 On the other hand,
the 31P NMR spectrum of the solution at −73.7 °C indicated only a
signal at ␦ = −41.6 with 1J(PtP) = 1482 Hz due to the presence of the
complex [PtMe2(dppm)] in solution. At −63.5 °C, the signal at ␦ =
0.88 ppm displayed platinum satellites with 2J(PtH) = 71 Hz, typical
for the starting platinum(II) complex 1a. The chemical shift of the
SnMe2Cl2 signal increased to ␦ = 1.16 ppm with 2J(119/117SnH) = 87 Hz
at −41.2 °C; however, the Pt−Me signal appeared at ␦ = 0.82 ppm
with a decreasing in the coupling constant of 2J(PtH) = 68 Hz.
Interestingly, there is a little increase in the chemical shift of the
Sn-Me signal of SnMe2Cl2 and a decrease in the 2J(119/117SnH) value
Reaction of [PtMe2(dppp)] with SnPh3Cl
A mixture of [PtMe2(dppp)] (90 mg, 0.14 mmol) and SnPh3Cl
(108 mg, 0.28 mmol) in acetone (20 mL) was stirred for 3 days. The
resultant white solid was filtered off and washed with diethyl
ether, identified as 2c. Yield: 51%.
Variable temperature NMR studies for the reaction of
[PtMe2(dppm)] with SnMe2Cl2
To a solution of solution of [PtMe2(dppm)] (15 mg, 0.025 mmol)
in acetone-d6 (0.5 mL) in an NMR tube, cooled to −84 °C, was added
SnMe2Cl2 (11 mg, 0.05 mmol). The tube was then placed in the
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1290
Can. J. Chem. Vol. 91, 2013
Fig. 1. Selected variable 1H NMR spectra (0.4–1.4 ppm) for the reaction of [PtMe2(dppm)] with SnMe2Cl2 in acetone-d6.
Scheme 2.
with increasing the temperature. For example, ␦ = 1.13 ppm with
2
2J(119/117SnH) = 91 Hz at −63.5 °C, ␦ = 1.15 ppm with J(119/117SnH) =
2
90 Hz at −50.0 °C, and ␦ = 1.16 ppm with J(119/117SnH) = 87 Hz at
−41.2 °C. Notably, at −39.4 °C, the magnitude of 2J(PtH) increased
to 73 Hz as well as the magnitude of 2J(119/117SnH), which increased
to 89 Hz. At this temperature, a small signal at ␦ = 0.60 ppm
appeared due to the formation of SnMe3Cl. At 0.2 °C, the spectrum
contained two very small doublets at ␦ = 0.76 ppm due to the
formation of [PtMeCl(dppm)] (2a). Note that at 6.4 °C, a very weak
signal appeared at ␦ = 0.50 due to the formation of the A-frame
dimer of [Pt2Me2(␮-Cl)(␮-dppm)2]Cl (4a).
At none of these temperatures could any platinum(IV) interme-
diate be detected by 31P and 1H NMR spectroscopy. Therefore, NMR
data show that the oxidative addition of SnMe2Cl2 to 1a occurs
very rapidly and the short-lived platinum(IV) intermediate is dif-
ficult to detect. The formation of the platinum(IV) intermediate
would lead to a decrease in the coupling constant of 2J(PtH). It can
be seen that the coupling constant of 2J(PtH) = 68 Hz reached a
minimum at −41.2 °C. At the same time, there is an increase in the
coupling constant of 2J(SnH) from 87.2 to 89.4 Hz at −39.4 °C. That
is suggested to be due to the oxidative addition of SnMe2Cl2 to 1a
to form a very unstable intermediate [PtMe2(dppm)(SnMe2Cl)Cl],
which could not be observed. At this temperature, the signal due
to the formation of SnMe3Cl resulting from the coupling of Sn−C
could be observed. It should be noted that there has been no
evidence for the elimination of ethane. Therefore, the coupling of
Sn(sp3)−C(sp3) is preferred relative to C(sp3)−C(sp3) coupling. On
the basis of the NMR data, we suggest a mechanism that involves the
unstable intermediate A, as shown in Scheme 2.
spectroscopy from the reactions of 1b and 1c with SnMe2Cl2. The
complexes 1b and 1c were too insoluble to provide satisfactory
variable-temperature NMR spectra.
The reaction of [PtMe2(PP)] (1a–1c) with SnPh3Cl afforded the
corresponding complexes [PtMeCl(PP)] (PP = dppm (2a), dppe (2b),
or dppp (2c)) as well as the complex [Pt2Me2(␮-Cl)(␮-dppm)2]Cl (4a)
in the case of dppm (Scheme 3). NMR data showed that the start-
ing complexes of 1a–1c were in the solution to some extent after a
reaction time of 2 days. However, these signals disappeared after
a reaction time of 3 days. The 1H NMR spectrum of the reaction of
1a with SnPh3Cl displayed a signal at ␦ = 0.60 ppm with tin satel-
lites, which were not well resolved. This signal is assigned to the
SnPh3Me resulting from the coupling of the Sn−C bond.30 The
1H NMR resonance for SnPh3Me in the reactions of 1b and 1c with
SnPh3Cl are mainly obscured by the more intense resonances of
Pt−Me bonds of [PtMeCl(PP)] (2b and 2c) flanked by both platinum
and phosphorus satellites.
In the course of work on the effect of the molar ratios of the
reactants, the reaction of [PtMe2(dppm)] with SnMe2Cl2 at a molar
ratio of 1:1 was complicated, containing the presence of several
unknown platinum(II) complexes in solution. In addition, the
complex of [PtCl2(dppm)] was obtained from the reaction of com-
plex 1a with SnMe2Cl2 at a Pt:Sn 1:20 molar ratio. On the other
hand, the reaction of 1a with SnPh3Cl at a Pt:Sn 1:20 molar ratio
The reaction of [PtMe2(PP)] (PP = dppe, dppp) (1b–1c) with
SnMe2Cl2 in a 1:2 Pt:Sn molar ratio proceeded similarly but in the
case of 1b, the only product was [PtMeCl(dppe)] (2b) (Scheme 1).
Compound SnMe3Cl could also be detected in situ by 1H NMR
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Momeni and Eatezadi
1291
Scheme 3.
Acknowledgement
We would like to thank the Science Research Council of K.N.
Toosi University of Technology for financial support.
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