Heterobimetallic Re-Pd, Re-Au and Re-Cu complexes derived from diphenylphosphino cyrhetrene: Synthesis and X-ray structure

Article abstract of DOI:10.1016/j.poly.2008.10.038

Diphenylphosphinecyrhetrene ligand (η⁵-C₅H₄PPh₂)Re(CO)₃ (1) reacts with 1 equiv. of PdCl₂(NCPh)₂ to form, after workup, the square-planar trans-[(η⁵-C₅H

Full text of DOI:10.1016/j.poly.2008.10.038

Polyhedron 28 (2009) 322–326
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Polyhedron
journal homepage: www.elsevier.com/locate/poly
Heterobimetallic Re–Pd, Re–Au and Re–Cu complexes derived from
diphenylphosphino cyrhetrene: Synthesis and X-ray structure
b
Diego Sierra a, Andres Muñoz a, Fernando Godoy a, A. Hugo Klahn a, , Andres Ibañez ,
*
M. Teresa Garland b, Mauricio Fuentealba b
a Instituto de Quimica, Pontificia Universidad Catolica de Valparaíso, Casilla 4059, Valparaíso, Chile
b CIMAT, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Casilla 653, Santiago, Chile
a r t i c l e i n f o
a b s t r a c t
Article history:
Diphenylphosphinecyrhetrene ligand (
g
5-C5H4PPh2)Re(CO)3 (1) reacts with 1 equiv. of PdCl2(NCPh)2 to
5-C5H4PPh2)Re(CO)3]PdCl2(NCMe) (2). Similarly, reaction
Received 3 September 2008
Accepted 27 October 2008
Available online 4 December 2008
form, after workup, the square-planar trans-[(
of
with (tetrahydrothiophene)AuCl produces, in excellent yield, the bimetallic complex [(g5
C5H4PPh2)Re(CO)3]AuCl (3) with a linear P–Au–Cl moiety. From the reaction of 2 equiv. of 1 with
CuBr(SMe2) the planar-trigonal complex [(
5-C5H4PPh2)Re(CO)3]2CuBr (4) was obtained. 31P NMR and
X-ray crystallography demonstrate, for the three cases, that (
5-C5H4PPh2)Re(CO)3 acts as a monodentate
g
1
-
g
Keywords:
Cyrhetrenyldiphenylphosphine ligand
Palladium
Gold
Copper
g
ligand. The structural parameters of the bimetallic complexes are compared with related diphenylphos-
phinoferrocene metal complexes, described in the literature.
Ó 2008 Elsevier Ltd. All rights reserved.
Complexes
1. Introduction
palladium-base catalytic system for Suzuki coupling reactions,
the bimetallic Re–Pd complex, which is probably involved in the
The diphenylphosphinocyclopentadienyl group
g
5-coordinated
catalytic system, was neither isolated nor characterized in situ.
to metal fragments has proved to be a versatile unsymmetrical
mono- or bidentate ligand to form homo- and heterobimetallic
complexes [1–3]. Complexes of this type include those which have
two metal centers of a very different nature (for example, early and
late transition metals) held together through a bridging ligand [4,5]
or both a bridging ligand and a metal–metal bond [6–9]. The most
common synthetic approach to form simple bridging bimetallic
compounds has been to bind first the cyclopentadienyl moiety to
one of the transition metals, thus producing a metallo ligand deriv-
ative, which may then act as a monodentate phosphorous ligand
The lack of information about the coordination chemistry of (g5
-
C5H4PPh2)Re(CO)3 (1) and the unknown structural data for bime-
tallic complexes containing this metallo ligand, encouraged us to
prepare and fully characterize by spectroscopic and crystallo-
graphic techniques the square-planar trans-[(
CO)3]PdCl2(NCMe) (2), linear [(
5-C5H4PPh2)Re(CO)3]AuCl (3) and
trigonal [(
5-C5H4PPh2)Re(CO)3]2CuBr (4) complexes.
g
5-C5H4PPh2)Re(-
g
g
2. Results and discussion
[4,5]. Several examples of metallo ligands of the type (g5
-
The preparation of diphenylphosphinocyclopentadienyl rhe-
nium tricarbonyl (1) was carried out according to the Gladysz pro-
cedure [12]. Bimetallic complex (2) is formed by the reaction of
C5H4PPh2)MLn, M = Fe, Ti, Zr, Co, Mo, Rh, etc. have been used to
prepare a large number of bimetallic complexes with interesting
chemical, electrochemical and catalytic properties [1,2,10]. Never-
theless, examples of group 7 metallo ligands remain relatively
(g
5-C5H4PPh2)Re(CO)3 with commercially available PdCl2(NCPh)2
(1:1 molar ratio) in CHCl3 under reflux for 4 h. Upon cooling the
mixture to room temperature, a red solid is formed which was
slightly soluble in chloroform but soluble in MeCN. Crystallization
from MeCN–Et2O yielded orange-red microcrystals of 2 (Scheme
1).
unexplored. (g
5-C5H4PPh2)M(CO)3 M = Mn and Re, were first re-
ported by Rausch and Spink in 1989 [11] by reaction of diph-
enylphosphinocyclopentadienylthallium with BrM(CO)5. Much
more recently, Gladysz and co-workers [12] prepared
C5H4PR2)Re(CO)3, R = Ph and tert-Bu, by direct reaction of (CpLi)R-
( -
g5
This reaction probably involves in a first step, the formation of
the chloro-bridged dimeric complex [Pd(l-Cl)Cl(g
5-C5H4PPh2)-
e(CO)3 with PR2Cl. Although, the phenyl derivative was used in a
Re(CO)3]2 which then, in the crystallization step, reacts with MeCN
to form the observed product. We were unable to characterize the
red solid in solution; nevertheless, the elemental analysis is consis-
tent with the proposed formula. Similar palladium chloro-bridged
* Corresponding author. Tel.: +56 32 2273174; fax: +56 32 2273422.
E-mail address: hklahn@ucv.cl (A. Hugo Klahn).
0277-5387/$ - see front matter Ó 2008 Elsevier Ltd. All rights reserved.
doi:10.1016/j.poly.2008.10.038

D. Sierra et al. / Polyhedron 28 (2009) 322–326
323
PPh2
Pd
PPh2
Ph2P
Au
The small downfield shift from that of the parent ligand (
is comparable to those found in other three-coordinated com-
plexes of copper(I) [20,21].
D
d = 3.5)
Cl
PdCl2(NCPh)2
AuCl(THT)
Re
Re
Re
Cl
CO
Cl
NCMe
OC
OC
OC
CO
CO
CO
CO
CO
2
1
3
3. X-ray crystallography
CuBr(SMe2
)
The numbering scheme of the bimetallic Re–Pd complex 2 is
presented in Fig. 1. Crystallographic data are presented in Table
1, whereas selected bond lengths and angles are shown in Table
2. In complex 2 the palladium atom exhibits a slightly distorted
CO
CO
OC
Br
Re
Cu
PPh2
Ph2P
square-planar geometry which is supported by (i) the displace-
0
ment of palladium atom by 0.06 ÅA away from the PNCl2 least-
squares plane and (ii) the sum of the four angles around the palla-
dium atom which is 361°. The phosphine and the acetonitrile li-
gand are found in a trans orientation with angles P(1)–Pd–N(1)
175.71°(15), Cl(1)–Pd–Cl(2) 171.25°(9). In the phosphine ligand
the phosphorous atom is tetrahedrally surrounded by the two phe-
nyl rings (P–C(14) = 1.808(5) Å and P–C(15) = 1.827(6) Å), and the
cyrhetrenyl ligand (P–C(1) = 1.807(5) Å). The latter distance com-
pares well to 1.803(3) Å found in (trans-[PdMeCl(PPh2Fc)2],
(PPh2Fc = ferrocenyldiphenylphosphine) [14]. The bond length
Pd–P (2.2217(13) Å) is quite short when compare to the similar
distance measured in related phosphinoferrocene complexes
(trans-[PdMeCl(PPh2Fc)2], Pd–P = 2.3328(10) Å [14] trans-[PdCl2-
(PPh3)2] Pd–P = 2.337(1) Å [22] but it resembles to the one ob-
Re
OC
CO
CO
4
Scheme 1.
complexes containing the phosphinoferrocene ligand have been re-
ported [13–15].
Compound 2 is air and moisture stable and moderately soluble
in polar organic solvents and insoluble in non polar solvents. The
elemental analysis of this compound is in good agreement with
the proposed structure. The 1H NMR spectrum (in CD3CN) of 2
showed in addition to the resonances of the metallo ligand, the
presence of coordinated MeCN as a singlet at d 1.98. The m(CN)
absorption band observed at 2297 cmꢀ1 (KBr disc) in the IR spec-
trum is further evidence for coordinated MeCN. A single resonance
in the 31P NMR spectrum indicates a single phosphorous environ-
ment due to the presence of the metallo ligand. This resonance is
shifted to lower field when compared to the free ligand
served in the dimer trans-[Pd(l-Cl)Me(PPh2Fc)]2 (avg. 2.223(9) Å)
[13]. The Pd–N bond length (2.085(5) Å) compares well with those
obtained for other square-planar Pd(II) complexes containing coor-
dinated acetonitrile with
a trans P–Pd–N moiety, such as
(MeCN)PdCl2( -dpmp)PdCl2 [23].
l
(Dd = 38.3). Similar shift have been observed in analogous palla-
dium complexes possessing the diphenylphosphinoferrocene li-
gand [14].
The C–P–Pd angles are all larger than the ideal 109.5°, and range
from 110.48(17)° to 118.25(18)°, while all C–P–C are smaller than
expected for normal tetrahedra, i.e. 101.3(2)–104.5(2)°. Similar
deviation has been reported for related Pd-complexes and ex-
plained in term of the valence shell electron pair repulsion theory
[14,24].
The molecular structure of complex 3 is shown in Fig. 2 and se-
lected bond distances and angles are presented in Table 2. Taking
into account the gold(I) environment this compound exhibits a
very regular linear geometry, with a P–Au–Cl angle of 178.24(4)°
The Re–Au bimetallic complex (3) was formed by reacting the
ligand 1 with the recommended gold precursor chloro(tetrahydro-
thiophene)gold(I) [16] in CH2Cl2, at room temperature (Scheme 1).
It was isolated as white crystals in 90% yield. The mass spectrum
and elemental analysis of this compound agrees well with the
presence of a single cyrhetrenylphosphine.
The 1H NMR spectrum of this complex showed, apart from the
multiplet from the phenyl protons, the signal of the cyrhetrenyl
unit as two multiplets for the cyclopentadienyl protons ring. Like
the previous case, the phosphorous resonance (observed at d
25.7) in the 31P NMR spectrum is shifted to lower field upon coor-
dination to Au(I).
Dd = 42.7, this value is comparable to those ob-
served in diphenylphosphinoferrocenes coordinated to the Au–Cl
fragment [17,18].
With regard to the complex (4) and considering that the reac-
tion of copper(I) halide, with tertiary organo-phosphines gives a
wide range of products of variable stoichiometry and molecular
structure [19], we decided to carry out the reaction of CuBr(SMe2)
with an excess of ligand 1 (1:4 molar ratio) (Scheme 1). After over-
night stirring (in CH2Cl2 at room temperature) followed by solvent
evaporation, a white solid was obtained, which showed two reso-
nances in the 31P NMR spectrum (d ꢀ17.0 and d ꢀ13.5) due to
the presence of uncoordinated 1 and a new compound. Column
chromatography allowed the separation of the two compounds; a
mixture of CH2Cl2/hexane (1:1) moved unreacted 1 whereas the
new complex was eluted with acetone. The solid obtained after
evaporation of acetone showed the same spectroscopic parameters
as the one isolated from the direct reaction of 1 and CuBr(SMe2) in
a 2:1 molar ratio. From the latter procedure, complex 4, was iso-
lated as white crystals in 81% yield, after crystallization from
CH2Cl2/hexane. The elemental analysis of 4 is in good agreement
with the proposed structure. The 31P NMR spectrum of 4 is consis-
tent with the presence of a single compound in solution (d ꢀ13.5).
Fig. 1. ORTEP’s plots of complex
probability level.
2 with displacement ellipsoids at the 30%

324
D. Sierra et al. / Polyhedron 28 (2009) 322–326
Table 1
Summary of crystallographic data and structure refinement for 2, 3 and 4.
2
3
4
Empirical formula
C22H17Cl2NO3PPdRe
737.84
C20H14AuClO3PRe
751.90
C41H30BrCl2CuO6P2Re2
1267.34
Formula mass (g molꢀ1
)
Collection T (K)
Crystal system
Space group
a (Å)
298(2)
monoclinic
P21/c
14.3454(11)
8.9720(7)
150(2)
monoclinic
P21/c
9.414(3)
150(2)
monoclinic
C2/c
15.8267(7)
b (Å)
22.808(7)
17.8010(7)
c (Å)
18.8294(15)
98.0260(10)
2399.7(3)
10.359(3)
117.03
1981.3(10)
14.8485(7)
97.1780(10)
4150.5(3)
b (°)
V (Å3)
Z
4
4
4
Dcalc (g cmꢀ3
)
2.042
2.521
2.028
Crystal size (mm)
0.29 ꢁ 0.152 ꢁ 0.13
0.20 ꢁ 0.16 ꢁ 0.10
0.43 ꢁ 0.25 ꢁ 0.17
F(000)
1400
1376
2408
Absorption coefficient (mmꢀ1
)
semi-empirical from equivalents
0.452 and 0.305
2.18–28.08
full-matrix least-squares on F2
0.2653 and 0.0155
1.79–27.90
semi-empirical from equivalents
0.278 and 0.155
1.73–27.81
Maximum and minimum transmission
h Range (°)
Range h, k, l
Reflections collected
ꢀ18/18, ꢀ11/11, ꢀ23/24
ꢀ11/11, ꢀ28/29, ꢀ13/13
ꢀ20/20, ꢀ22/23, ꢀ19/18
19649
20673
17275
Independent reflections (Rint
Data/restraints/parameters
)
5417 (0.0365)
5417/0/281
R1 = 0.0385, wR2 = 0.0845
R1 = 0.0478, wR2 = 0.0885
1.084
4432 (0.1052)
4432/0/244
R1 = 0.0261, wR2 = 0.0655
R1 = 0.0284, wR2 = 0.0667
1.067
4730 (0.0369)
4730/0/250
R1 = 0.0319, wR2 = 0.0849
R1 = 0.0379, wR2 = 0.0889
1.061
Final R indices [I > 2
R indices (all data)
r
(I)]
Goodness of fit on F2
Largest difference in peak and hole (e Aꢀ3
)
1.729 and ꢀ0.554
1.657 and ꢀ2.174
2.662 and ꢀ1.396
Table 2
Select bond lengths (Å) and bond angles (°) for 2, 3 and 4.
2
3
4
Bond distances
Re–C(6)
Re–C(7)
1.909(7)
1.914(7)
1.916(6)
1.952
1.807(5)
2.2217(13)
2.2734(19)
2.2952(15)
2.086(5)
1.918(5)
1.941(5)
1.895(5)
1.956
1.791(4)
2.2214(13)
2.2798(13)
1.913(5)
1.918(5)
1.923(5)
1.961
1.802(4)
2.2346(11)
2.3416(10)
Re–C(8)
Re–Cp(centroid)
C(1)–P(1)
M–P(1)
M–X(1)
M–X(2)
M–N
Bond angles
Re–C(6)–O(1)
Re–C(7)–O(2)
Re–C(8)–O(3)
C(1)–P(1)–M
C(9)–P(1)–C(15)
P(1)–M–X(1)
P(1)–M–X(2)
P(1)–M–N(1)
P(1)–M–P(1)#
177.0(6)
177.0(6)
176.5(6)
116.56(17)
110.40(16)
93.56(6)
88.36(5)
175.67(14)
177.5(4)
176.6(4)
177.5(4)
112.03(16)
107.7(2)
178.24(4)
176.8(5)
177.8(5)
178.4(5)
114.44(15)
103.7(2)
119.87(3)
120.26(6)
Fig. 2. ORTEP’s plots of complex
3
with displacement ellipsoids at the 30%
probability level.
which is slightly larger to those found in related ferrocenyl phos-
phine derivatives, for example, 177.12(10)° in AuCl(PPh2Fc), [17]
176.1(1)° in AuCl(PPhFc2) [25] and 176.01(7)° in AuCl(PPh2CH2Fc)
[26]. The Au–Cl and Au–P bond distances of 2.2798(13) Å and
2.2214(13) Å are similar to the ones measured in AuCl(PPh2Fc)
and AuCl(PPhFc2) [17,25]. The shortest gold–gold distance in the
lattice is 6.640 Å, which excludes the possibility of any bonding
interaction between gold atoms.
Crystals of complex 4 were obtained from a of CH2Cl2/hexane
mixture (1:5) at room temperature. A view of the molecular struc-
ture is presented in Fig. 3 with the relevant interatomic distances
and angles summarized in Table 2. The coordination geometry
about the copper atom is almost idealized trigonal planar accord-
ing to (i) the negligible displacement of copper atom away from
the P2Br plane and (ii) the sum of the three angles around the cop-
per atom which is 360°. These two last observations are conse-
quences of symmetry operator (C2 axis) in the Cu–Br bond. The
bulky cyrhetrenyl groups adopt an anti conformation respect to
the trigonal plane. The Cu–Br distance of 2.3416(10) Å is compara-
ble to those observed in other three-coordinated copper(I) com-
pounds [20,21,27]. The Cu–P distance of 2.2346(11) Å is
somewhat shorter than that measured previously in copper(I) bro-
mide complexes containing tertiary organo-phosphines [20,21,27].
Within the cyrhetrenyl group the average Re–Cp (centroid) and
Re–C(O) distances and Re–C–O angles are comparable to the one
observed in complexes 2 and 3, and are also concordant with the
corresponding values reported for other complexes containing
the cyrhetrenyl group [28–30].

D. Sierra et al. / Polyhedron 28 (2009) 322–326
325
4.2. [(g
5-C5H4PPh2)Re(CO)3]AuCl (3)
To a solution of 1 (100 mg, 0.193 mmol) dissolved in 10 mL of
CH2Cl2 were slowly added 61 mg (0.193 mmol) of (tht)AuCl dis-
solved in 5 mL of CH2Cl2. The transparent mixture was stirred at
room temperature for 4 h. Solvent was pumped off and the color-
less oil produced was crystallized from CH2Cl2/hexane (1.5) to give
white crystals of 3 (130 mg, 0.173 mmol, 90%).
IR (cmꢀ1, CH2Cl2) m(CO) 2032 (s); 1942 (vs). 1H NMR (CDCl3) d:
5,56 (m, 2H, C5H4), 5,69 (m, 2H, C5H4), 7.48–7.62 (m, 10H, C6H5).
31P{1H} NMR (CDCl3) d: 25.7 (s, PPh2). Mass spectrum (187Re and
35Cl) m/z: 752 [M+], 520 [M+ꢀAuCl], 492 [M+ꢀAuClꢀCO], 435
[M+ꢀAuClꢀ3CO]. Elemental Anal. Calc. for C20H14O3PClReAu: C,
31.87; H, 1.86. Found: C, 31.92; H, 1.90%.
4.3. [(g
5-C5H4PPh2)Re(CO)3]2CuBr (4)
To a solution of ligand 1 (120 mg, 0.231 mmol) in 15 mL of
CH2Cl2 were added 24 mg (0.115 mmol) of solid CuBr(Sme2). The
pale purple suspension formed was stirred overnight at room tem-
perature. After this time the mixture became a colorless solution.
Solvent evaporation to dryness produced a white solid which
was crystallized from CH2Cl2/hexane (1:5) generating transparent
crystals of complex 4 (112 mg, 0.095 mmol, 81%).
Fig. 3. ORTEP’s plots of complex
probability level.
4 with displacement ellipsoids at the 30%
IR (cmꢀ1, CH2Cl2) m(CO) 2028 (s); 1933 (vs). 1H NMR (CDCl3) d:
5.36 (broad signal, 2H, C5H4), 5.86 (broad signal, 2H, C5H4), 7.28–
7.40 (m, 10H, C6H5). 31P{1H} NMR (CDCl3) d: ꢀ13.5 (broad signal,
PPh2). Elemental Anal. Calc. for C40H28O6P2BrReCu: C, 40.54; H,
2.36. Found: C, 40.39; H, 2.35.
4. Experimental
4.4. X-ray crystal structure determination of complexes 2, 3 and 4
All reactions were carried out under nitrogen atmosphere
using standard Schlenk techniques. Solvents were purified as fol-
low: hexane and tetrahydrofuran by distillation from sodium/
benzophenone ketyl; dichloromethane, chloroform and acetoni-
trile by distillation from P2O5. PdCl2(NCPh)2 and CuBr(SMe2)
Single crystals of complexes 2, 3 and 4, obtained as mentioned
above, were mounted on the tip of a glass fiber in a random orienta-
tion. Intensity data were collected on a Bruker Smart Apex diffrac-
(Aldrich) were use as received. (g
5-C5H4PPh2)Re(CO)3 (1) [12]
tometer equipped with
graphite monochromated Mo K
empirical corrections, via -scans, were applied for absorption for
a
bidimensional CCD detector using
a
radiation (k = 0.71073 Å). Semi-
and (tht)AuCl (tht = tetrahydrothiophene) [16] were prepared fol-
lowing published procedures. Infrared spectra were recorded with
a Perkin–Elmer FT-IR Spectrum One spectrophotometer. NMR
spectra were recorded with a Bruker Avance 400 spectrometer.
1H NMR chemical shifts were referenced using the chemicals
shifts of residual solvent resonances, and 31P{1H}NMR chemical
shifts were referenced to 85% H3PO4 as external standard. The
mass spectrum of 3 was obtained on a Thermo-Finnigan MAT
900XP, at the Facultad de Ciencias Químicas y Farmacéuticas,
Universidad de Chile.
w
complexes 2 and 3, and face indexing absorption correction was ap-
plied to complex 4. The diffraction frames were integrated using the
SAINT package [31] and corrected for absorption with XPREP in SHELXTL-PC
[32] and SADABS [33]. The structures were solved using XS in SHELXTL-PC
[32] by direct methods and completed (non-H atoms) by difference
Fourier techniques. Refinement was performed by the full-matrix
least-squares method based on F2. All non-hydrogen atoms were
anisotropically refined. Hydrogen atoms were placed in their calcu-
lated positions, assigned fixed isotropic thermal parameters and al-
lowed to ride on their respective parent atoms. A summary of the
data collectionand structure refinement parameters is given in Table
1. ORTEP plots of complexes 2, 3 and 4 with displacement ellipsoids
at the 30% probability level were generated with XP in SHELXTL-PC [32].
4.1. trans-[(
g
5-C5H4PPh2)Re(CO)3]PdCl2(NCMe) (2)
To 60 mg (0.116 mmol) of (
g
5-C5H4PPh2)Re(CO)3 (1) dissolved
in 15 mL of chloroform were added 44 mg (0.115 mmol) of solid
PdCl2(NCPh)2 and the mixture was refluxed for 4 h. After cooling
at room temperature a red precipitate was formed, this was filtered
out and washed with chloroform. The elemental analysis of this
material reveals a dimeric nature (Anal. Calc. for [C20H14O3PCl2-
RePd]2 ꢂ CHCl3: C, 32.52; H, 1.91. Found: C, 32,49; H, 1.89%). Crys-
tallization from acetonitrile/diethylether (1:3) yielded orange-red
microcrystals (suitable for analysis of X-ray diffraction) of 2
(62 mg, 0,084 mmol, 73%).
Acknowledgements
A.H.K. acknowledges FONDECYT (Project 1060487) and D.I. Pon-
tificia Universidad Catolica de Valparaiso. D.S. acknowledges
MECESUP and FONDECYT for a Doctoral scholarship. We also
appreciate the financial support of MECESUP (Project UCH 0116)
for a MS instrument. The loan of NH4ReO4 from MOLYMET-Chile
is also much appreciated.
IR (cmꢀ1, CH3CN) m(CO) 2029 (s); 1936 (vs). IR (cmꢀ1, KBr) m(CN)
2297 m(CO) 2032 (s); 1943 (vs); 1933 (vs). 1H NMR (CD3CN) d:
1.98 (s, 3H, CH3CN), 5.60 (m, 2H, C5H4), 5.81 (m, 2H, C5H4), 7.50–
7.74 (m, 10H, C6H5). 31P{1H} NMR (CD3CN) d: 21,3 (s, PPh2). Ele-
mental Anal. Calc. for C22H17O3NPCl2RePd: C, 35.87; H, 2.31. Found:
C, 35.79; H, 2.30%.
Appendix A. Supplementary data
CCDC 692241, 692242 and 692243 contain the supplementary
crystallographic data for complexes 2, 3 and 4. These data can be

326
D. Sierra et al. / Polyhedron 28 (2009) 322–326
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