Inorganica Chimica Acta 429 (2015) 4650

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Inorganica Chimica Acta

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Palladium(II) complexes of anthraquinone-based AsOAs type

and SeOSe type bipodands. Synthesis, X-ray crystallography
and catalytic properties
Kadarkaraisamy Mariappan , Janani Sindhu Ragothaman, Vinothini Balasubramanian, Mariah Hoffman,
Madhubabu Alaparthi, Andrew G. Sykes
Department of Chemistry, University of South Dakota, Vermillion, SD 57069, United States

a r t i c l e

i n f o

Article history:
Received 8 September 2014
Received in revised form 9 December 2014
Accepted 10 December 2014
Available online 7 February 2015
This work is dedicated to Dr. A.
Shumugasundaram, Retired professor,
Department of Chemistry at Virudhunagar
Hindu Nadars Senthikumara Nadar College,
Virudhunagar, Tamilnadu, India.

a b s t r a c t
The reaction of the Ph2As anion with 1,8-bis(2-bromoethoxy)anthracene-9,10-dione in 2:1 ratio generates 1,8-bis(2-diphenylarsinoethoxy)anthracene-9,10-dione (L1). L1 and 1,8-bis(2-phenylselenoethoxy)anthraquinone (L2) reacted with bis(benzonitrile)palladium(II) chloride in 1:1 ratio yielding
Pd(L1)Cl2 (1) and Pd(L2)Cl2 (2). X-ray structures of 1 and 2 revealed that L1 and L2 chelate with Pd(II)
and form a convex square planar geometry. The catalytic properties of both Pd(II) complexes in the Heck
reaction was investigated, and the results show that compound 2 acts as a better catalyst than 1. The
redox behavior of L1, 1 and 2 versus Ag/AgCl are also explored.
2015 Elsevier B.V. All rights reserved.

Keywords:
Anthraquinone
Diphenylarsino ligand
Palladium complex

1. Introduction
Anthraquinone (AQ)-based ligands and their metal complexes
are a rich eld of study due to their multifarious applications.
[1]. We have recently reported the selective chelation of nitrogen
[2a,b], sulfur [2c] and selenium derivatives [2d] of 1,8-disubstituted anthraquinone to Ag(I) and Cu(I). The selenium derivative
served also as chemodosimeter for the detection of Cu(II) and
Fe(III). Making of complexes of platinum group elements with a
variety of ligands particularly hemilabile ligands, is one of the
hot elds in coordination chemistry due to the catalytic properties
of Pd(II), Rh(III) and Ru(II) complexes in many organic reactions.
The hemilabile ligands [3] have the capacity to tune the catalytic
activity of a metal center due to their temporary possession of
the coordination site before they are substituted by a substrate
in the sequence of a catalytic reaction. Ligands with mixed donors
(phosphorous/oxygen; phosphorus/nitrogen) type have been especially useful for the design of catalytically active species [4] and
have found application in many reactions. There are numerous
Corresponding author.
E-mail address: Kadarkaraisamy.Mariappan@usd.edu (K. Mariappan).
http://dx.doi.org/10.1016/j.ica.2014.12.028
0020-1693/ 2015 Elsevier B.V. All rights reserved.

hemilabile arsenic donors that have been studied along with their
coordination chemistry [5a] in the literature; but there is a scarcity
of arsenic complexes that are known as catalysts [5b].
Many methods are available to construct the carboncarbon
bond, which is crucial for all of organic chemistry, but specically
the assembly of CarylCaryl bonds in diverse natural products, medicinal agents, and organic materials. Transition metal-catalyzed
cross-couplings to form CarylCaryl bonds are widely used in traditional synthetic methods [6] such as the SuzukiMiyaura reaction,
the Stille reaction, the Kumada reaction, and Negishi reaction. The
Heck reaction is another powerful method, and this reaction uses
Pd(0)/Pd(II) complexes as catalysts. Most of the palladium complexes used for the Heck reaction contain either palladacycles or
palladium complex by electron-rich ligands like phosphine or
includes pnictogens and chalcogens as donors [7]. It was therefore
thought worthwhile to synthesize anthraquinone based palladium
complexes with AsOAs or SeOSe as electron donors and study
their catalytic properties. We report here the synthesize of L1 (As
OAs), the complexation behavior of L1 and L2 (SeOSe) with palladium(II) including the X-ray structures of [PdCl2(L1)] and
[PdCl2(L2)]. The catalytic efcacy of both Pd(II) complexes in the
Heck reaction is also explored.

K. Mariappan et al. / Inorganica Chimica Acta 429 (2015) 4650

2. Experimental
2.1. Materials and methods
1,8-bis(2-bromoethoxy)anthracene-9,10-dione [8] and 1,8bis(2-phenylselenoethoxy)anthracene-9,10-dione (L2) [2b] were
synthesized by earlier available literature. Pd(PhCN)2Cl2 was also
synthesized by an available procedure [9]. Triphenylarsine, lithium
metal, tetrabutylammonium hexauorophosphate and 2-chloro-2methylpropane were purchased from Aldrich and used without
purication. CH3CN, THF, DMF and CH2Cl2 were purchased from
Aldrich and puried using PURE SOLV solvent purication system. 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were
obtained on Bruker 400 MHz instrument at room temperature
using deuterated solvents. Absorbance data were collected using
a HP 8452A diode array spectrophotometer and Varian Cary 50
BIO. Luminescence titrations were conducted using a SPEX Fluoromax uorimeter. Mass spectrometry was conducted using a Varian
500-MS IT ESI mass spectrometer. Elemental analyses were conducted using an Exeter CE-440 Elemental analyzer. Melting points
were determined using open capillaries and were uncorrected.
Cyclic voltammograms were recorded in a CH instruments 660
electrochemical workstation using dry methylene chloride as solvent and tetrabutylammonium hexauorophosphate as electrolyte
under nitrogen atmosphere.
X-ray quality crystals of compounds 1 and 2 were obtained by
slow evaporation of a CHCl3:CH3OH solution. Crystallographic data
for 1 and 2 were collected at 100 K using a Bruker SMART APEX II
diffractometer using Mo Ka radiation. Data reduction and renement were completed using the WinGX suite of crystallographic
software [10,11]. Structures were solved using OLEX [12]. All hydrogen atoms were placed in ideal positions and rened as riding
atoms with relative isotropic displacement parameters. Table 1
lists additional crystallographic and renement information.
2.2. Synthesis
2.2.1. Synthesis of 1,8-bis(2-diphenylarsinoethoxy)anthracene-9,10dione (L1)
Triphenylarsine (0.5 g, 1.62 mmol) was dissolved in 50 mL of
dry THF under a nitrogen atmosphere. A red solution was obtained
several minutes after adding excess lithium metal to the triphenylarsine solution. The solution was stirred for 3 h, and the red solution was transferred into another clean, dry ask using a cannula
under nitrogen atmosphere, and mixed with 2-chloro-2-methylpropane (0.15 g, 1.62 mmol) in THF to destroy unwanted PhLi. A
solution of 1,8-bis(2-bromoethoxy)anthracene-9,10-dione (0.37 g,
0.81 mmol) made in 30 mL of THF was added to the red (Ph)2As
and the solution was stirred for 3 h. THF was evaporated under
reduced pressure and the residue was puried by a silica gel column using methylene chloride: ethyl acetate mixture as eluent.
The yield is 0.35 g (28%) as yellow brous solid, and the melting
point is 137140 C. Elemental Anal. Calc. for C42H34O4As2: C,
67.03; H, 4.55. Found: C, 66.94; H, 4.47%. ESI-MS: Calculated for
sodiated species (1+Na+): 775.57; Found 775.48.
1
H NMR (at 25 C, CDCl3): d 2.602.64 (t, J = 8 Hz, 4H, CH2-As);
4.284.32 (t, J = 8 Hz, 4H, CH2-O); 7.087.10 (d, 2H, ArH from
AQ); 7.247.30 (m, 10H, ArH from phenyl ring); 7.427.52 (m,
12H, ArH from phenyl ring); 7.767.78 (d, 2H, ArH from AQ).
13
C NMR (at 25 C, CDCl3): 27.1; 67.7; 119.1; 119.9; 124.8;
128.5; 128.7; 132.9; 133.5; 134.8; 139.4; 158.2; 182.2; 184.0.
2.2.2. Synthesis of Pd(L1)Cl2 (1)
L1 (0.1 g, 0.133 mmol) was dissolved in 10 mL of methylene
chloride and mixed with a solution containing 0.051 g

47

(0.133 mmol) of Pd(PhCN)2Cl2 in 10 mL of methylene chloride.

The solution was stirred for 2 h and all the solvents were evaporated. The residue was dissolved in chloroform: methanol (8:2) mixture and evaporated slowly. Red-orange block shaped crystals
were obtained. The yield is 0.08 g of red orange blocks crystals that
were isolated (64%) and melting point is above 160 C (dec).
Elemental Anal. Calc. for C42H34O4As2PdCl2: C, 54.24; H, 3.66.
Found: C, 54.57; H, 3.70%.
1
H NMR (at 25 C, CDCl3): d 3.123.16 (t, J = 8 Hz, 4H, CH2-As);
4.004.04 (t, J = 8 Hz, 4H, CH2-O); 6.936.95 (d, 2H, ArH from
AQ); 7.247.37 (m, 10H, ArH from phenyl ring); 7.497.53 (t, 2H,
ArH from AQ); 7.787.80 (m, 10H, ArH from phenyl ring); 7.85
7.87 (d, 2H, ArH from AQ).
13
C NMR (at 25 C, CDCl3): 22.7, 64.7, 117.8, 119.2, 128.6, 129.9,
131.0, 133.4, 133.7, 157.8, 181.2. All the peaks are very short even
after running 5000 plus scans due to solubility issues.
2.2.3. Synthesis of Pd(L2)Cl2 (2)
L2 (0.1 g, 0.163 mmol) was used instead of L1 to synthesize 2
with an identical procedure (0.063 g Pd(PhCN)2Cl2, 0.163 mmol)
to 1 and crystallized using CHCl3CH3OH. Yield is 0.09 g (69%) of
dark red blocks crystals that were isolated and started decomposed
above 210 C. Elemental Anal. Calc. for C30H24O4Se2PdCl2: C, 45.97;
H, 3.06. Found: C, 45.28; H, 2.96%.
1
H NMR (at 25 C, CDCl3): d 2.822.88 (m, 2H, CH2-Se); 4.33
4.65 (m, 4H, CH2-O); 4.814.87 (m, 2H, CH2-Se); 7.128.08 (m,
8H, ArH from AQ + Phenyl ring); 7.527.61 (m, 6H, ArH from
AQ + Phenyl ring); 7.827.86 (d, 2H, ArH from AQ).
13
C NMR (at 25 C, CDCl3): 32.4, 66.6, 118.1, 119.2, 120.1, 129.7,
133.2, 133.7, 134.7, 183.9. All the peaks are very short even after
running 5000 plus scans due to solubility issue.
2.2.4. Catalytic properties of 1 and 2
Method A: A slight modication is done on a method available
in literature [13c]. A mixture of styrene (0.104 g, 1 mmol), bromobenzene (0.157 g, 1 mmol), DMF (5 mL), and complex 1 or 2
in catalytic amounts (0.001 g, 0.001 mmol) was heated at
100 C under inert atmosphere in the presence of a base (0.118 g,
2 mmol of propyl amine) for 24 h. Stilbene formation was conrmed by LC and GC mass spectrometry.
Method B: We were inspired by an literature report [7a] and
adopted the following method. A mixture of styrene (0.208 g,
2 mmol), bromobenzene (0.157 g, 1 mmol), n-butylamine
(0.146 g, 2 mmol), p-xylene (3 mL) and complex 1 or 2 in catalytic quantities (0.001 g, 0.001 mmol) was reuxed 24 h. Stilbene
was isolated as the product after working up the reaction using
methylene chloride and dilute acid. Stilbene formation was conrmed by GC MS.
Yield when using 1 as catalyst: 0%. Yield when using 2 as catalyst: 1020%. Stilbene yield is based on bromobenzene.
3. Results and discussion
3.1. Synthesis and NMR spectroscopy
The reaction of 1,8-bis(2-bromoethoxy)anthracene-9,10-dione
with diphenylarsino anion in THF under nitrogen (Scheme 1) gives
L1 in 18% yield. Compound L1 is fully stable under ambient condition and soluble in common organic solvents. The 1H NMR spectrum of L1 has a doublet, a triplet and a doublet in the aromatic
region due to 1,8-oxydisubstitued anthraquinone derivative, and
triplets for CH2-O and CH2-As appear at 4.30 (J = 8 Hz) and 2.62
(J = 8 Hz) respectively, in the aliphatic region. 13C NMR spectrum
CH2-O and CH2-As signals appear at 67.8 ppm and 27.1 ppm. We
observe two shorter peaks at 182.2 and 184.0 ppm that are due

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K. Mariappan et al. / Inorganica Chimica Acta 429 (2015) 4650

O

Se

Se

Ph2As-

PhSe-

EtOH, N2

O
Br

As

As

Br

L2
L

THF, N2

Pd(PhCN)2Cl2

L1

CH2Cl2
Pd(L)Cl2

Scheme 1. Synthesis of ligand L1, L2 and their palladium complexes.

Fig. 1. Molecular structure of 1 (A) and 2 (B). Hydrogen atoms are not labeled. L1 and L2 formed a fourteen membered a buttery outline with Pd(II) (C). Slightly convex
square planar geometry of Pd(II) in 1 is shown as insets (D).

Table 2
Selected bond lengths () and bond angles () of 1 and 2. E = As in 1 and Se in 2.
Table 1
Crystallographic data for 1 and 2.

Empirical formula
Wavelength
System
Temperature (K)
Crystal system
Space group
a ()
b ()
c ()
a ()
b ()
c ()
Volume (3)
Z
Dcalc (g cm 3)
Absorbtion coefcient
(mm 1)
F(0 0 0)
h range
Index ranges
Reections collected
Independent reections
Observed reections
Maximum/minimum
transition
Data/
restraints/parameters
Goodness-of-t
Final R1 indices[I > 2r(I)]
R1 indices (all data)
CCDC Number

C42H34As2O4 PdCl2
Mo Ka 0.71073
SMART APEXII
100(2)
monoclinic
P21/n
10.9673(9)
20.3071(16)
17.0490(14)
90.00
105.5790(10)
90.00
3657.6(5)
4
1.689
2.492

C30H24Se2O4PdCl2
Mo Ka 0.71073
SMART APEXII
293(2)
monoclinic
P21/n
10.3549(5)
16.4489(8)
32.2860(16)
90.00
92.0430(10)
90.00
5495.7(5)
8
1.894
3.556

1856
2.1725.47
h( 13,13), k( 24,24),
l( 20,20)
36 346
6784
5481
0.478/0.608

3072
1.7725.38
h( 12,12), k( 19,19),
l( 38,38)
54 609
10 104
9117
0.020.33

6784/0/460

10 104/0/703

1.026
0.0259
0.0403
1004317

1.097
0.0253
0.0300
1004318

C16E1
C18E2
C7O1 (C@O)
C8O2 (C@O)
PdE1
PdE2
PdCl1
PdCl2
C16E1Pd
C18E2Pd
E1PdE2
ClPdCl2

1.955(3)
1.952(3)
1.229(3)
1.222(4)
2.3889(4)
2.3999(4)
2.3186(7)
2.3140(7)
120.60(9)
114.93(9
168.332(14)
175.24(3)

1.970(3)
1.972(3)
1.224(4)
1.219(3)
2.4252(3)
2.4336(4)
2.2923(7)
2.3052(8)
110.43(9)
108.64(9)
170.427(14)
174.06(3)

to the two carbonyl groups in L1. The poor solubility of 1 and 2 in

CDCl3 and in other deuterated solvent prevented a quality 13C
NMR.
In the Pd(II) complex 1, the CH2-As signal in L1 deshielded by
0.5 ppm (SI Fig. 5) and CH2-Se signal in L2 shifted by 0.3 ppm in
the 1H NMR spectra. These shifts support the interaction of arsenic
and selenium with Pd(II). 1H and 13C NMR of L1, L2, 1 and 2 (SI
Figs. 17) and LC MS of L1 (SI Fig. 8) are given as supplementary
material. NMR spectroscopic data, elemental analyses are in good
agreement with the structures and stoichiometry of L1, L2, 1 and
2 proposed in Scheme 1.
3.2. X-ray crystallography
The molecular structures of 1 and 2 are shown in Fig 1. Crystallographic data for both 1 and 2 are given in Table 1, and selected

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K. Mariappan et al. / Inorganica Chimica Acta 429 (2015) 4650

Br

1 or 2

Base, Solvent
Scheme 2. Heck Reaction.

bond lengths and bond angles are given in Table 2. L1 and L2 acted
as chelators and both pnictogenide and chalcogenide donors are
trans to each other in 1 and 2. The PdAs bond lengths [Pd
As1 = 2.3889(4) ; PdAs2 is 2.3999(4) ] are similar to one another and match the literature [13a]. Typical PdCl interatomic [13b]
distance average is 2.262.33 , and PdCl bond length in 1 also
matches [PdCl1 = 2.3186(7) ; PdCl2 = 2.3140(7) ] an earlier
report [7a,13c]. In our previous reports [2], the intraannular carbonyl group was involved in bonding; however, in 1 the carbonyl
oxygen is not involved in making a coordinate bond with Pd(II).
The arsenic atoms in 1 have a distorted tetrahedral geometry
and palladium(II) has a convex square planar geometry, which is
clearly reected in the bond angles [As1PdAs2 (168.332(14);
Cl1PdCl2 (175.24(3)] around Pd(II). The improper square planar
geometry of Pd(II) may be due to crowded arsenic donors.
The thermal ellipsoid diagram for 2 is shown in Fig. 1B. In 2, the
PdSe bond lengths [PdSe1 = 2.4252(3) ; PdSe2 is 2.4336(4) ],
and the PdCl bond lengths are [PdCl1 = 2.2923(7) ; Pd
Cl2 = 2.3052(8) ] very similar to one another, and compare well
with literature as well as 1 [7a,13c]. Like 1, the intraannular carbonyl group in 2 is not involved in forming a coordinate covalent
bond with Pd(II). The selenium atoms in 2 have T shaped geometries and palladium(II) has a convex square planar geometry like
1, but in 2, the Pd(II) geometry is closer to square which is clearly
observed in the bond angles [Se1PdSe2 (170.427(14); Cl1Pd
Cl2 (174.06(3)] around Pd(II).
3.3. Catalytic applications of 1 and 2
Pd(II) complexes especially with selenium donors [7] have
shown catalytic properties for the Heck reaction in the recent past,
and these reports inspired us to study the catalytic properties of 1
and 2 for the Heck reaction as per Scheme 2 [13c]. The catalytic
properties were studied using 0.001 mol% concentration of 1 and
2 in presence of a base. Compound 2 was able to convert styrene
into stilbene (1020 yield) in both methods [SI Figs. 9 and 10]
whereas compound 1 produced no stilbene [SI Fig. 10]. The solution color changed from yellow-orange into brown/black after
heating when 1 was used as catalyst, and this may be due to the
formation of palladium nanoparticles [14] by decomposition of 1
in the course of the reaction. The crowded Pd(II) centers and formation of palladium NPs may be the reason for the non-catalytic
activity of 1. Having higher mol% of 1 did not improve the yield
of stilbene, and we are currently working on improving catalytic

Fig. 2. Cyclic voltammogram of 1 in dry CH2Cl2 using 0.1 M TBAH vs. Ag/AgCl on
glassy carbon.

performance by synthesizing phosphorous analogue of L1 since

phosphorous ligand containing complexes are well known catalyst.
3.4. Cyclic voltammetry
The redox electrochemistries of L1, 1 and 2 were investigated
by means of cyclic voltammetry. Cyclic voltammetric measurements were carried out in 0.1 M tetrabutylammonium hexauorophosphate (TBAH) using dry CH2Cl2 as solvent versus Ag/
AgCl as the reference electrode under inert atmosphere. The anodic
and cathodic peaks were used to calculate the E0 values that are
listed in Table 3. Compounds L1 ( 0.984 V and 1.298 V), L2
( 1.007 V & 1.297 V), 1 ( 1.001 V & 1.297 V) and 2 ( 0.995 V
& 1.299 V) show two reversible couple, and we attribute those
redox potentials to the anthraquinone [2c,d] moiety. L1, L2 and
the palladium complexes, 1 and 2 exhibit characteristic irreversible
oxidation peaks for arsenide and selenide [2d,15,16] moieties at
+1.528, +1.224, +1.65 and +0.99 V, respectively, as expected. Palladium complexes 1, 2 produced additional irreversible reduction
peaks at 0.911 V and 0.732 V respectively, and an irreversible
oxidation peak at +0.61. We attribute these peaks may be due to
the palladium [17] metal center. Cyclic voltammogram of 1 is
shown in Fig. 2. Cyclic voltammograms of triphenylarsine,
Pd(PhCN)4Cl2 and 2 in dry methylene chloride are given in SI
Fig. 11.
4. Conclusions
A unique AsOAs ligand 1,8-bis(2-diphenylarsinoethoxy)anthracene-9,10-dione (L1) has been prepared successfully; this is
rst AQ-bipodand that contains arsenic as donors. L1 and 1,8bis(2-phenylselenoethoxy)anthracene-9,10-dione (L2) react with
bis(benzonitrile)palladium(II) chloride to form Pd(II) complexes
with the stoichiometry [PdCl2(L1)] and [PdCl2(L2)]. Relatively long

Table 3
Electrochemical data.
Compounds

Ea1/2 (V)
Anthraquinone0/

L1
L2
1
2

0.984
1.007
1.001
0.995

Anthraquinone
1.298
1.235
1.297
1.299

1/ 2

Arsenic/selenium oxidation

Oxidation

Reduction

1.528b
1.224b
1.65b
0.99b

+0.62
Not observedc

All measurements were done at room temperature using dry methylene chloride as solvent under inert atmosphere.
a
Referenced vs. Ag/AgCl, glassy carbon, 1 mM in 0.1 M TBAH.
b
Irreversible.
c
Might be merged with selenium oxidation peak.

0.911b
0.732b

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K. Mariappan et al. / Inorganica Chimica Acta 429 (2015) 4650

PdAs and PdSe bond lengths are possibly due to the trans inuence of donor atoms on Pd(II). Both L1 and L2 form palladacycles
with 14 atoms in a ring, and Pd(II) roughly having a square planar
geometries. Compound 2 shows a higher catalytic activity towards
the Heck reaction than compound 1 and which may be due to its
inability to withstand high temperature which might be leading
the formation of PdSe NPs as well crowded palladium center of 1.
Acknowledgements

[4]

[5]

[6]

Authors J.S.R. and K.M. greatly appreciate nancial support from

NSF Northern Plains Research Experience for Undergraduates
(CHE-1063000), United States. NSF-EPSCoR (EPS-0554609) and
the South Dakota Governors 2010 Initiative are appreciated on
account of the purchase of a Bruker SMART APEX II CCD diffractometer. NSF-URC (CHE 0532242), United States also provided
funding for the purchase of elemental analyzer.
[7]

Appendix A. Supplementary material

CCDC 1004317 (1) and 1004318 (2) contain the supplementary
crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data_request/cif. Supplementary data
associated with this article can be found, in the online version, at
http://dx.doi.org/10.1016/j.ica.2014.12.028.
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